469:
492:. For that reason, the efficiency of this enzyme is dependent on the activity of DszD and on environmental oxygenation. The reaction catalyzed by DszC involves three phases: 1) molecular oxygen activation leading to the formation of a hydroperoxyflavin-intermediate (C4aOOH); 2) oxidation of DBT to DBTO; and 3) dehydration of FMN. DszC is the second least efficient enzyme in the pathway with a particularly low
510:
258:
949:
Directive 2009/30/EC of the
European Parliament and of the Council of 23 April 2009 amending Directive 98/70/EC as regards the specification of petrol, diesel and gas-oil and introducing a mechanism to monitor and reduce greenhouse gas emissions and amending Council Directive 1999/32/EC as regards
318:
and the remaining of the substrate. Since the end products of the pathway are still water soluble sulfur compounds, the pathway has often been disregarded as an appealing pathway for industrial applications, in particular by the oil industry. The most well-studied sulfur specific pathway is the 4S
592:
for the wild-type 4S pathway enzymes is low when compared to the rate that needs to be achieved for a viable application in the industrial sector. An increase of 500-fold on the overall rate of the pathway is the required improvement for an efficient application of this biodesulfurization method.
529:
At last, the desulfinase (DszB) cleaves the remaining carbon-sulfur bond in 2-hydroxybiphenyl-2-sulfinate converting it into the sulfur-free 2-hydroxybiphenyl in a two step mechanism. In the first, and rate-limiting, step, 2-hydroxybiphenyl-2-sulfinate is protonated by Cys27 in its electrophilic
667:
of HBP to the protein revealed that HBP forms a π-interaction with Trp327, thus inhibiting DszC. The A101K/W327C (AKWC) double mutant revealed to be desensitized to low HBP concentrations and the bacterial strain expressing the AKWC DszC was 14-fold more efficient than the wild-type strain.
166:
per year. Furthermore, these processes usually require large amounts of energy, and are accompanied by massive costs for the industries that employ them. A greener and also complementary alternative process to the conventional desulfurization methods is biodesulfurization.
229:
There are two main pathways through which bacteria remove sulfur from sulfur-containing compounds: ring destructive pathways and sulfur-specific pathways. The ring destructive pathway consists of the selective cleavage of carbon-carbon bonds with release of small
603:
or a combination of both strategies are some of the approaches that have been applied to tackle the lack of catalytic efficiency and stability of the 4S enzymes. The 4S pathway best improvement to date was obtained by a directed evolution approach in which
525:
provided by DszD and molecular oxygen for its catalytic cycle. Nonetheless, the reaction rate of DszA is about seven times faster than DszC. However, like DszC, it suffers feedback inhibition by the final product of the pathway, 2-HBP.
501:
of 1.6 ± 0.3 min. It is also severely affected from feedback inhibition caused mostly by HPBS and 2-HBP, the products of DszA and DszB respectively, For that reason, it has been targeted for optimization through
136:, while the US has made efforts to restrict the sulfur content in diesel and gasoline to a maximum of 15 ppm. The reduction of sulfur compounds in oil fuels can be achieved by a process named
202:. To date, pilot attempts for industrial applications have resorted to the use of whole bacterial systems, because biodesulfurization involves a sequential cascade of reactions by different
724:. The Thr62 mutation by an Asp residue returns the lowest activation energy from all possible mutants at this position due to the stabilization effect induced by Asp negative charge.
705:
DszD has also been targeted for rate enhancing mutation on the Thr62 residue. Mutation of Thr62 by Asn and Ala residues managed to increase its activity 5- and 7-fold, respectively.
2012:
Sousa, Sérgio F.; Sousa, Joana F. M.; Barbosa, Ana C. C.; Ferreira, Cleide E.; Neves, Rui P. P.; Ribeiro, António J. M.; Fernandes, Pedro A.; Ramos, Maria João (July 14, 2016).
124:
The reduction of the concentration of sulfur in crude oil becomes necessary to mitigate one of the leading sources of the harmful health and environmental effects caused by its
879:
2155:"Improved Efficiency of the Desulfurization of Oil Sulfur Compounds in Escherichia coli Using a Combination of Desensitization Engineering and DszC Overexpression"
379:
234:
soluble in the surrounding aqueous environment, whereas the sulfur-specific pathways rely on successive sulfur redox reactions to release sulfur either as
2116:"Enhancement of desulfurization activity by enzymes of the Rhodococcus dsz operon through coexpression of a high sulfur peptide and directed evolution"
699:
679:
of the 4S pathway. A computational rational design approach determined a set of mutations that could accelerate the charge transfer occurring in the
2153:
Li, Lu; Liao, Yibo; Luo, Yifan; Zhang, Guangming; Liao, Xihao; Zhang, Wei; Zheng, Suiping; Han, Shuangyan; Lin, Ying; Liang, Shuli (June 21, 2019).
155:
Despite their efficiency at reducing sulfur content, the conventional desulfurization methods are still accountable for a significant amount of the
2014:"Improving the Biodesulfurization of Crude Oil and Derivatives: A QM/MM Investigation of the Catalytic Mechanism of NADH-FMN Oxidoreductase (DszD)"
198:
Biodesulfurization is an attractive alternative to sulfur removal, particularly in the crude oil fractions where there is an abundance of sulfur
1523:
1446:
925:
2208:
OHSHIRO, Takashi; OHKITA, Ryo; TAKIKAWA, Takeshi; MANABE, Masanori; LEE, Woo Cheol; TANOKURA, Masaru; IZUMI, Yoshikazu (November 23, 2007).
647:
of DszC was also tackled by a combination of directed evolution and rational design approach to desensitize DszC to the 4S pathway product,
58:. Depending on its source, the amount of sulfur present in crude oil can range from 0.05 to 10%. Accordingly, the oil can be classified as
214:
either with the sulfur atom or molecular oxygen. However, they lacked the scalability desired for an industrial setup due to overall low
1748:"Desulphurisation of benzothiophene and dibenzothiophene by actinomycete organisms belonging to the genus Rhodococcus, and related taxa"
2210:"Improvement of 2′-Hydroxybiphenyl-2-sulfinate Desulfinase, an Enzyme Involved in the Dibenzothiophene Desulfurization Pathway, from
717:
558:
450:
296:
242:
anions as byproducts. The latter have thus been considered as a very promising pathway to produce sulfur-free compounds with a high
1204:
Miranda-Galindo, Erick Yair; Segovia-Hernández, Juan
Gabriel; Hernández, Salvador; Bonilla-Petriciolet, Adrián (October 22, 2014).
2114:
Pan, Jie; Wu, Fan; Wang, Jia; Yu, Linqing; Khayyat, Naghmeh
Hassanzadeh; Stark, Benjamin C.; Kilbane, John J. (October 1, 2013).
1248:
Boniek, Douglas; Figueiredo, Débora; dos Santos, Antônio
Fernando Batista; de Resende Stoianoff, Maria Aparecida (January 2015).
702:
approach, the Y63F/Q65H double mutant revealed an increase in the enzyme's thermostability without loss of catalytic efficiency.
546:. DszB is the least efficient enzyme on the pathway making it an appealing target for enhancement through protein engineering.
1295:
Gunam, Ida Bagus Wayan; Yaku, Yosuke; Hirano, Makoto; Yamamura, Kenta; Tomita, Fusao; Sone, Teruo; Asano, Kozo (April 2006).
1798:"Elucidation of the metabolic pathway for dibenzothiophene desulphurization by Rhodococcus sp. strain IGTS8 (ATCC 53968)"
2271:"Site-directed mutagenesis enhances the activity of NADH-FMN oxidoreductase (DszD) activity of Rhodococcus erythropolis"
573:
moiety of the oxidized FMN forming FMNH. In the second step, a water molecule protonates the N1 atom of FMNH giving FMNH
2369:
1545:
Kodama, Koki; Umehara, Kazuyoshi; Shimizu, Katsumi; Nakatani, Shigeru; Minoda, Yasuji; Yamada, Koichi (January 1973).
721:
1967:"Reaction Mechanism and Determinants for Efficient Catalysis by DszB, a Key Enzyme for Crude Oil Bio-desulfurization"
950:
the specification of fuel used by inland waterway vessels and repealing
Directive 93/12/EEC (Text with EEA relevance)
1796:
Oldfield, Christopher; Pogrebinsky, Olga; Simmonds, Julie; Olson, Edwin S.; Kulpa, Charles F. (September 1, 1997).
468:
114:
972:
1380:"The bacterial 4S pathway – an economical alternative for crude oil desulphurization that r educes CO2 emissions"
709:
614:
476:
DszC is the first enzyme to intervene in the pathway in two sequential steps, catalyzing the double oxidation of
1915:
Barbosa, Ana C. C.; Neves, Rui P. P.; Sousa, Sérgio F.; Ramos, Maria J.; Fernandes, Pedro A. (October 5, 2018).
1965:
Sousa, João P. M.; Neves, Rui P. P.; Sousa, Sérgio F.; Ramos, Maria J.; Fernandes, Pedro A. (August 21, 2020).
1681:
Abin-Fuentes, Andres; Mohamed, Magdy El-Said; Wang, Daniel I. C.; Prather, Kristala L. J. (December 15, 2013).
676:
320:
266:
81:, which are harmful to public health and contribute to serious environmental effects such as air pollution and
1206:"Multiobjective Optimization of a Hydrodesulfurization Process of Diesel Using Distillation with Side Reactor"
1297:"Biodesulfurization of alkylated forms of dibenzothiophene and benzothiophene by Sphingomonas subarctica T7b"
485:
207:
2326:"Improving the Catalytic Power of the DszD Enzyme for the Biodesulfurization of Crude Oil and Derivatives"
118:
1746:
Oldfield, Christopher; Wood, Nicola T.; Gilbert, Steven C.; Murray, Frazer D.; Faure, Fabrice R. (1998).
391:
199:
2269:
Kamali, Nasrin; Tavallaie, Mahmood; Bambai, Bijan; Karkhane, Ali Asghar; Miri, Mandana (July 1, 2010).
1030:"Science and technology of novel processes for deep desulfurization of oil refinery streams: a review☆"
999:"Science and technology of novel processes for deep desulfurization of oil refinery streams: a review⋆"
880:"An Introduction to Petroleum Refining and the Production of Ultra Low Sulfur Gasoline and Diesel Fuel"
226:
would be desirable, known implementations are still well below the efficiency met for whole-cell ones.
2115:
2068:
1029:
2025:
1694:
629:
215:
141:
1378:
Sousa, João P. M.; Ferreira, Pedro; Neves, Rui P. P.; Ramos, Maria J.; Fernandes, Pedro A. (2020).
664:
503:
265:
The most studied ring destructive pathway is the Kodama pathway and it was initially identified in
793:
222:
mechanisms and toxicity, or inadequate conditions for long-term bacterial growth. While cell-free
2306:
2251:
2190:
1994:
1944:
1885:
1866:
1775:
1644:
1469:
1426:
1407:
1335:
1296:
1277:
1186:
1139:
998:
905:
849:
821:
759:
684:
596:
398:
243:
133:
94:
86:
1547:"Identification of Microbial Products from Dibenzothiophene and Its Proposed Oxidation Pathway"
521:, converting DBT-sulfone into 2-hydroxybiphenyl-2-sulfinate. Like DszC, DszA also requires FMNH
2345:
2324:
Ferreira, Pedro; Sousa, Sérgio F.; Fernandes, Pedro A.; Ramos, Maria João (December 6, 2017).
2298:
2290:
2243:
2235:
2182:
2174:
2135:
2096:
2088:
2049:
2041:
1986:
1936:
1917:"Mechanistic Studies of a Flavin Monooxygenase: Sulfur Oxidation of Dibenzothiophenes by DszC"
1827:
1819:
1767:
1728:
1710:
1625:
1607:
1566:
1519:
1442:
1399:
1355:
1316:
1269:
1227:
1178:
1131:
1049:
921:
813:
688:
430:
231:
2325:
2337:
2282:
2225:
2166:
2127:
2080:
2033:
1978:
1928:
1897:
1858:
1809:
1759:
1718:
1702:
1656:
1615:
1597:
1558:
1511:
1481:
1434:
1391:
1347:
1336:"Biodesulfurization of dibenzothiophene by a newly isolated Rhodococcus erythropolis strain"
1308:
1261:
1217:
1170:
1121:
1088:
1080:
1067:
Campos-Martin, J.M.; Capel-Sanchez, M.C.; Perez-Presas, P.; Fierro, J.L.G. (March 9, 2010).
1041:
1010:
913:
861:
805:
771:
633:
610:
517:
DszA is responsible for the third step of the pathway. It catalyzes the first carbon-sulfur
477:
438:
402:
327:
219:
47:
1645:"Biodesulfurization potential of a newly isolated bacterium, Gordonia alkanivorans RIPI90A"
1158:
2374:
1546:
733:
695:
672:
600:
586:
493:
434:
406:
292:
247:
223:
137:
59:
1503:
2029:
1698:
1427:"Chapter 2 Petroleum biorefining: the selective removal of sulfur, nitrogen, and metals"
1250:"Biodesulfurization: a mini review about the immediate search for the future technology"
1068:
906:"Chapter 2 Petroleum biorefining: the selective removal of sulfur, nitrogen, and metals"
1723:
1682:
1620:
1585:
648:
557:
cofactor needed for the reactions catalyzed by DszC and DszA, through the oxidation of
550:
442:
359:
251:
156:
129:
63:
1901:
1485:
1438:
1045:
1014:
917:
775:
195:
and their derivatives, were observed to constitute important substrates for bacteria.
46:
Crude oil contains sulfur in its composition, with the latter being the most abundant
2363:
2194:
2154:
1998:
1948:
1411:
1281:
1249:
1190:
589:
570:
518:
280:
31:
2310:
2255:
2013:
1966:
1916:
1886:"Evaluation of sulfate-reducing bacteria for desulfurizing bitumen or its fractions"
1870:
1779:
1660:
1174:
1143:
825:
1846:
1747:
1562:
1351:
1334:
Davoodi-Dehaghani, Fatemeh; Vosoughi, Manouchehr; Ziaee, Abed Ali (February 2010).
656:
566:
457:
and a fourth to regenerate the FMN-oxide byproduct of DszA) and three molecules of
418:
315:
175:
It has been observed that there are sulfur-dependent bacteria that make use of the
149:
70:
1515:
509:
2084:
1157:
Hosseini, Alireza; Khoshsima, Ali; Sabzi, Mazaher; Rostam, Ata (April 21, 2022).
809:
1814:
1797:
1683:"Exploring the Mechanism of Biocatalyst Inhibition in Microbial Desulfurization"
865:
680:
606:
534:. In the second step, a water molecule is deprotonated by Cys27 followed by the
414:
284:
188:
106:
102:
98:
2131:
947:
530:
carbon leading to the cleavage of the carbon-sulfur bond and displacement of SO
179:
in sulfur-containing compounds in their life cycles (either in their growth or
162:
emissions associated with the crude oil refining process, releasing up to 9000
2286:
2170:
1862:
1763:
1265:
1126:
1109:
462:
383:
311:
180:
125:
78:
2294:
2239:
2178:
2139:
2092:
2045:
2037:
1990:
1982:
1940:
1932:
1823:
1714:
1611:
1570:
1403:
1273:
1231:
1182:
1135:
1053:
817:
708:
A computational study demonstrated that substitutions in position 62 of DszD
2270:
850:"Biodesulfurization of diesel fuels – Past, present and future perspectives"
660:
535:
375:
351:
343:
335:
303:
192:
90:
82:
27:
2349:
2341:
2302:
2247:
2186:
2100:
2053:
1884:
Armstrong, Stephen M.; Sankey, Bruce M.; Voordouw, Gerrit (February 1997).
1771:
1732:
1629:
1359:
1320:
1159:"Toward Application of Ionic Liquids to Desulfurization of Fuels: A Review"
306:
promoting ring cleavage and formation of a pyruvyl branch; concluding with
257:
1831:
1602:
1706:
671:
DszB, the final enzyme in the pathway, is also one of the slowest with a
644:
110:
55:
1312:
1395:
1379:
1093:
713:
618:
562:
446:
410:
367:
363:
339:
239:
235:
2230:
2209:
1510:, Berlin, Heidelberg: Springer Berlin Heidelberg, pp. 2129–2141,
1222:
1205:
1084:
101:
catalysts. The levels of sulfur in any oil field are too high for the
85:. In addition, the sulfur content in crude oil is a major problem for
652:
625:
489:
458:
387:
203:
184:
176:
51:
35:
23:
480:
first into DBT-sulfoxide and then into DBT-sulfone. It requires FMNH
390:, DszD, which is responsible for the regeneration and supply of the
467:
211:
163:
145:
132:
has taken steps to decrease the sulfur content in diesel below 10
66:
if the sulfur concentration is below or above 0.5%, respectively.
1590:
International
Journal of Environmental Research and Public Health
1643:
Mohebali, G.; Ball, A.S.; Rasekh, B.; Kaytash, A. (March 2007).
561:
to NAD in a two step mechanism. The first step corresponds to a
370:
are required for the process: three of which are encoded in the
794:"API Gravity, Sulfur Content, and Desulfurization of Crude Oil"
792:
Demirbas, A.; Alidrisi, H.; Balubaid, M. A. (January 2, 2015).
691:
for the reaction and potentially increasing its turnover rate.
148:
desulfurization, extractive desulfurization, and extraction by
1847:"Biodegradation of dibenzothiophene by thermophilic bacteria"
1497:
1495:
2069:"Microbial biocatalyst developments to upgrade fossil fuels"
1584:
Seo, Jong-Su; Keum, Young-Soo; Li, Qing (January 13, 2009).
1470:"Whole cell biocatalysis for an oil desulfurization process"
1502:
Borgne, S. Le; Ayala, M. (2010), Timmis, Kenneth N. (ed.),
760:"Biotechnological processes for the refining of petroleum"
401:
can use an alternative sulfur-specific pathway to produce
140:. Methods used for desulfurization include, among others,
1504:"Microorganisms Utilizing Sulfur-Containing Hydrocarbons"
1468:
Setti, L.; Lanzarini, G.; Pifferi, P.G. (November 1997).
753:
751:
749:
287:
of the carbons in one of the aromatic rings, followed by
1069:"Oxidative processes of desulfurization of liquid fuels"
1845:
Bahrami, A.; Shojaosadati, S.A.; Mohebali, G. (2001).
712:
have a major impact in the activation energy for the
2075:. Environmental biotechnology/Energy biotechnology.
1243:
1241:
854:
1073:Journal of Chemical Technology & Biotechnology
628:(which encodes for DszA, DszB and DszC). After 40
453:molecules (three required by DszD to generate FMNH
848:Mohebali, Ghasemali; Ball, Andrew S. (May 2016).
787:
785:
758:Borgne, Sylvie Le; Quintero, Rodolfo (May 2003).
651:. The bacterial strain expressing the DszC A101K
1373:
1371:
1369:
183:), producing molecules with lower/no content in
1960:
1958:
1210:Industrial & Engineering Chemistry Research
843:
841:
839:
837:
835:
1508:Handbook of Hydrocarbon and Lipid Microbiology
1108:Javadli, Rashad; de Klerk, Arno (March 2012).
569:moiety of NADH to the central nitrogen in the
171:Biodesulfurization implementation and pathways
1586:"Bacterial Degradation of Aromatic Compounds"
1028:Babich, I. V; Moulijn, J. A (April 1, 2003).
884:International Council on Clean Transportation
8:
472:General chemical equation of the 4S pathway.
2218:Bioscience, Biotechnology, and Biochemistry
1433:, vol. 151, Elsevier, pp. 29–65,
1254:Clean Technologies and Environmental Policy
912:, vol. 151, Elsevier, pp. 29–65,
488:, which is supplied by DszD, and molecular
326:, which was observed to remove sulfur from
319:pathway, first discovered in the bacterium
16:Biotechnique to clean sulfur from crude oil
350:a carbon-sulfur bond cleavage by a second
2229:
1813:
1722:
1619:
1601:
1221:
1125:
1092:
640:strains presented a 35-fold improvement.
636:was the sole sulfur source, the modified
275:. The pathway comprises four main steps:
261:The Kodama and the 4S bacterial pathways.
1431:Studies in Surface Science and Catalysis
1301:Journal of Bioscience and Bioengineering
910:Studies in Surface Science and Catalysis
508:
256:
973:"Diesel Fuel Standards and Rulemakings"
745:
1687:Applied and Environmental Microbiology
314:of the pyruvyl substituent to release
2214:KA2-5-1 by Site-Directed Mutagenesis"
1791:
1789:
1676:
1674:
1672:
1670:
1551:Agricultural and Biological Chemistry
1425:Kilbane, J.J.; Le Borgne, S. (2004),
904:Kilbane, J.J.; Le Borgne, S. (2004),
358:desulfination reaction through which
334:a double oxidation of the sulfur (to
69:The combustion of crude oil releases
7:
429:The 4S pathway is a sulfur-specific
397:It has also been observed that some
2018:The Journal of Physical Chemistry A
675:of 1.7 ± 0.2 min, becoming a major
250:of sulfur heterocycles abundant in
105:derived from it (such as gasoline,
461:, thus producing NAD and water as
14:
581:Engineering of 4S pathway enzymes
513:General scheme of the 4S pathway.
2073:Current Opinion in Biotechnology
2067:Kilbane, John J (June 1, 2006).
798:Petroleum Science and Technology
694:DszB's catalytic efficiency and
330:and derivatives in three steps:
117:without pre-treatment to remove
1661:10.1016/j.enzmictec.2006.05.012
1649:Enzyme and Microbial Technology
1175:10.1021/acs.energyfuels.1c03974
405:instead. However, to date, the
2330:Chemistry – A European Journal
1563:10.1080/00021369.1973.10860640
1352:10.1016/j.biortech.2009.08.058
1114:Applied Petrochemical Research
1110:"Desulfurization of heavy oil"
971:US EPA, OAR (April 10, 2015).
953:, vol. OJ L, June 5, 2009
392:flavin mononucleotide cofactor
376:flavin-dependent monoxygenases
1:
1902:10.1016/S0016-2361(96)00226-8
1516:10.1007/978-3-540-77587-4_154
1486:10.1016/S0378-3820(97)00023-4
1439:10.1016/s0167-2991(04)80143-5
1046:10.1016/S0016-2361(02)00324-1
1015:10.1016/S0016-2361(02)00324-1
918:10.1016/s0167-2991(04)80143-5
776:10.1016/S0378-3820(03)00007-9
366:are produced. In total, four
352:flavin-dependent monoxygenase
344:flavin-dependent monoxygenase
2085:10.1016/j.copbio.2006.04.005
810:10.1080/10916466.2014.950383
632:events in a medium in which
394:required for DszA and DszC.
1815:10.1099/00221287-143-9-2961
866:10.1016/j.ibiod.2016.03.011
553:(DszD) regenerates the FMNH
285:NADH-dependent dioxygenases
22:is the process of removing
2391:
2132:10.1016/j.fuel.2013.04.065
1474:Fuel Processing Technology
764:Fuel Processing Technology
449:. It uses a total of four
421:oil has not been observed
2287:10.1007/s10529-010-0254-4
2171:10.1021/acssynbio.9b00126
1266:10.1007/s10098-014-0812-x
1127:10.1007/s13203-012-0006-6
698:was also addressed in an
93:of the equipment and the
2212:Rhodococcus erythropolis
2038:10.1021/acs.jpca.6b01536
1983:10.1021/acscatal.0c03122
1933:10.1021/acscatal.8b01877
997:Babich, I (April 2003).
700:experimental mutagenesis
322:Rhodococcus erythropolis
1863:10.1023/A:1010592615572
1764:10.1023/A:1001724516342
1752:Antonie van Leeuwenhoek
716:transfer reaction from
378:DszA and DszC, and the
268:Pseudomonas abikonensis
246:, in particular in the
2342:10.1002/chem.201704057
1340:Bioresource Technology
514:
473:
425:The aerobic 4S pathway
262:
206:and a large amount of
119:organosulfur compounds
2275:Biotechnology Letters
2159:ACS Synthetic Biology
1851:Biotechnology Letters
1603:10.3390/ijerph6010278
663:strain. Additionally
512:
471:
409:of fractions such as
260:
128:. In this sense, the
89:, as it promotes the
1707:10.1128/AEM.02696-13
621:encoding a modified
346:, followed by
142:hydrodesulfurization
2336:(68): 17231–17241.
2030:2016JPCA..120.5300S
1699:2013ApEnM..79.7807A
1313:10.1263/jbb.101.322
1216:(42): 16425–16435.
645:feedback inhibition
224:recombinant enzymes
220:feedback inhibition
181:metabolic processes
30:through the use of
2370:Chemical processes
1396:10.1039/D0GC02055A
1163:Energy & Fuels
685:reaction mechanism
597:Directed evolution
565:transfer from the
515:
504:enzyme engineering
474:
399:anaerobic bacteria
273:Pseudomonas jijani
263:
191:compounds, namely
115:combustion engines
20:Biodesulfurization
2231:10.1271/bbb.70436
2224:(11): 2815–2821.
2024:(27): 5300–5306.
1977:(16): 9545–9554.
1927:(10): 9298–9311.
1693:(24): 7807–7817.
1525:978-3-540-77584-3
1448:978-0-444-51699-2
1390:(22): 7604–7621.
1223:10.1021/ie501940v
1085:10.1002/jctb.2371
927:978-0-444-51699-2
689:activation energy
443:2-hydroxybiphenyl
431:metabolic pathway
382:DszB) and fourth
360:2-hydroxybiphenyl
342:) performed by a
328:dibenzothiophenes
295:of the ring by a
244:calorific content
216:enzyme efficiency
210:participating in
187:. In particular,
2382:
2354:
2353:
2321:
2315:
2314:
2266:
2260:
2259:
2233:
2205:
2199:
2198:
2165:(6): 1441–1451.
2150:
2144:
2143:
2111:
2105:
2104:
2064:
2058:
2057:
2009:
2003:
2002:
1962:
1953:
1952:
1912:
1906:
1905:
1881:
1875:
1874:
1842:
1836:
1835:
1817:
1808:(9): 2961–2973.
1793:
1784:
1783:
1758:(1/3): 119–132.
1743:
1737:
1736:
1726:
1678:
1665:
1664:
1640:
1634:
1633:
1623:
1605:
1581:
1575:
1574:
1542:
1536:
1535:
1534:
1532:
1499:
1490:
1489:
1480:(1–3): 145–153.
1465:
1459:
1458:
1457:
1455:
1422:
1416:
1415:
1375:
1364:
1363:
1346:(3): 1102–1105.
1331:
1325:
1324:
1292:
1286:
1285:
1245:
1236:
1235:
1225:
1201:
1195:
1194:
1169:(8): 4119–4152.
1154:
1148:
1147:
1129:
1105:
1099:
1098:
1096:
1064:
1058:
1057:
1025:
1019:
1018:
994:
988:
987:
985:
983:
968:
962:
961:
960:
958:
944:
938:
937:
936:
934:
901:
895:
894:
892:
890:
876:
870:
869:
845:
830:
829:
789:
780:
779:
755:
659:relative to the
439:dibenzothiophene
403:hydrogen sulfide
232:organic sulfides
113:) to be used in
2390:
2389:
2385:
2384:
2383:
2381:
2380:
2379:
2360:
2359:
2358:
2357:
2323:
2322:
2318:
2268:
2267:
2263:
2207:
2206:
2202:
2152:
2151:
2147:
2113:
2112:
2108:
2066:
2065:
2061:
2011:
2010:
2006:
1964:
1963:
1956:
1914:
1913:
1909:
1883:
1882:
1878:
1857:(11): 899–901.
1844:
1843:
1839:
1795:
1794:
1787:
1745:
1744:
1740:
1680:
1679:
1668:
1642:
1641:
1637:
1583:
1582:
1578:
1544:
1543:
1539:
1530:
1528:
1526:
1501:
1500:
1493:
1467:
1466:
1462:
1453:
1451:
1449:
1424:
1423:
1419:
1384:Green Chemistry
1377:
1376:
1367:
1333:
1332:
1328:
1294:
1293:
1289:
1247:
1246:
1239:
1203:
1202:
1198:
1156:
1155:
1151:
1107:
1106:
1102:
1066:
1065:
1061:
1027:
1026:
1022:
996:
995:
991:
981:
979:
970:
969:
965:
956:
954:
946:
945:
941:
932:
930:
928:
903:
902:
898:
888:
886:
878:
877:
873:
847:
846:
833:
791:
790:
783:
757:
756:
747:
742:
734:Desulfurization
730:
696:thermostability
687:, reducing the
601:rational design
587:desulfurization
583:
576:
556:
545:
541:
533:
524:
498:
483:
456:
435:desulfurization
427:
407:desulfurization
293:dehydrogenation
279:the successive
248:desulfurization
212:redox reactions
173:
160:
138:desulfurization
76:
44:
17:
12:
11:
5:
2388:
2386:
2378:
2377:
2372:
2362:
2361:
2356:
2355:
2316:
2281:(7): 921–927.
2261:
2200:
2145:
2106:
2079:(3): 305–314.
2059:
2004:
1954:
1907:
1896:(3): 223–227.
1876:
1837:
1785:
1738:
1666:
1655:(4): 578–584.
1635:
1596:(1): 278–309.
1576:
1537:
1524:
1491:
1460:
1447:
1417:
1365:
1326:
1307:(4): 322–327.
1287:
1237:
1196:
1149:
1100:
1079:(7): 879–890.
1059:
1040:(6): 607–631.
1020:
1009:(6): 607–631.
989:
963:
939:
926:
896:
871:
831:
781:
770:(2): 155–169.
744:
743:
741:
738:
737:
736:
729:
726:
655:showed higher
582:
579:
574:
554:
551:oxidoreductase
543:
539:
531:
522:
496:
481:
454:
437:that converts
426:
423:
415:vacuum gas oil
324:(strain IGTS8)
252:sour crude oil
189:heteroaromatic
172:
169:
158:
130:European Union
74:
43:
40:
32:microorganisms
15:
13:
10:
9:
6:
4:
3:
2:
2387:
2376:
2373:
2371:
2368:
2367:
2365:
2351:
2347:
2343:
2339:
2335:
2331:
2327:
2320:
2317:
2312:
2308:
2304:
2300:
2296:
2292:
2288:
2284:
2280:
2276:
2272:
2265:
2262:
2257:
2253:
2249:
2245:
2241:
2237:
2232:
2227:
2223:
2219:
2215:
2213:
2204:
2201:
2196:
2192:
2188:
2184:
2180:
2176:
2172:
2168:
2164:
2160:
2156:
2149:
2146:
2141:
2137:
2133:
2129:
2125:
2121:
2117:
2110:
2107:
2102:
2098:
2094:
2090:
2086:
2082:
2078:
2074:
2070:
2063:
2060:
2055:
2051:
2047:
2043:
2039:
2035:
2031:
2027:
2023:
2019:
2015:
2008:
2005:
2000:
1996:
1992:
1988:
1984:
1980:
1976:
1972:
1971:ACS Catalysis
1968:
1961:
1959:
1955:
1950:
1946:
1942:
1938:
1934:
1930:
1926:
1922:
1921:ACS Catalysis
1918:
1911:
1908:
1903:
1899:
1895:
1891:
1887:
1880:
1877:
1872:
1868:
1864:
1860:
1856:
1852:
1848:
1841:
1838:
1833:
1829:
1825:
1821:
1816:
1811:
1807:
1803:
1799:
1792:
1790:
1786:
1781:
1777:
1773:
1769:
1765:
1761:
1757:
1753:
1749:
1742:
1739:
1734:
1730:
1725:
1720:
1716:
1712:
1708:
1704:
1700:
1696:
1692:
1688:
1684:
1677:
1675:
1673:
1671:
1667:
1662:
1658:
1654:
1650:
1646:
1639:
1636:
1631:
1627:
1622:
1617:
1613:
1609:
1604:
1599:
1595:
1591:
1587:
1580:
1577:
1572:
1568:
1564:
1560:
1556:
1552:
1548:
1541:
1538:
1527:
1521:
1517:
1513:
1509:
1505:
1498:
1496:
1492:
1487:
1483:
1479:
1475:
1471:
1464:
1461:
1450:
1444:
1440:
1436:
1432:
1428:
1421:
1418:
1413:
1409:
1405:
1401:
1397:
1393:
1389:
1385:
1381:
1374:
1372:
1370:
1366:
1361:
1357:
1353:
1349:
1345:
1341:
1337:
1330:
1327:
1322:
1318:
1314:
1310:
1306:
1302:
1298:
1291:
1288:
1283:
1279:
1275:
1271:
1267:
1263:
1259:
1255:
1251:
1244:
1242:
1238:
1233:
1229:
1224:
1219:
1215:
1211:
1207:
1200:
1197:
1192:
1188:
1184:
1180:
1176:
1172:
1168:
1164:
1160:
1153:
1150:
1145:
1141:
1137:
1133:
1128:
1123:
1120:(1–4): 3–19.
1119:
1115:
1111:
1104:
1101:
1095:
1090:
1086:
1082:
1078:
1074:
1070:
1063:
1060:
1055:
1051:
1047:
1043:
1039:
1035:
1031:
1024:
1021:
1016:
1012:
1008:
1004:
1000:
993:
990:
978:
974:
967:
964:
952:
951:
943:
940:
929:
923:
919:
915:
911:
907:
900:
897:
885:
881:
875:
872:
867:
863:
859:
855:
851:
844:
842:
840:
838:
836:
832:
827:
823:
819:
815:
811:
807:
804:(1): 93–101.
803:
799:
795:
788:
786:
782:
777:
773:
769:
765:
761:
754:
752:
750:
746:
739:
735:
732:
731:
727:
725:
723:
719:
715:
711:
706:
703:
701:
697:
692:
690:
686:
682:
678:
674:
673:turnover rate
669:
666:
662:
658:
654:
650:
646:
641:
639:
635:
631:
627:
624:
620:
616:
612:
609:
608:
602:
598:
594:
591:
588:
580:
578:
572:
571:isoalloxazine
568:
564:
560:
552:
549:The NADH-FMN
547:
537:
527:
520:
519:bond cleavage
511:
507:
505:
500:
499:
491:
487:
479:
470:
466:
464:
460:
452:
448:
444:
440:
436:
433:of oxidative
432:
424:
422:
420:
416:
412:
408:
404:
400:
395:
393:
389:
385:
381:
377:
373:
369:
365:
361:
357:
353:
349:
345:
341:
337:
333:
329:
325:
323:
317:
313:
309:
305:
302:
298:
294:
290:
286:
282:
281:hydroxylation
278:
274:
270:
269:
259:
255:
253:
249:
245:
241:
237:
233:
227:
225:
221:
217:
213:
209:
205:
201:
196:
194:
190:
186:
182:
178:
170:
168:
165:
161:
153:
151:
150:ionic liquids
147:
143:
139:
135:
131:
127:
122:
120:
116:
112:
108:
104:
100:
96:
92:
88:
84:
80:
72:
71:sulfur oxides
67:
65:
61:
57:
53:
49:
41:
39:
37:
33:
29:
25:
21:
2333:
2329:
2319:
2278:
2274:
2264:
2221:
2217:
2211:
2203:
2162:
2158:
2148:
2123:
2119:
2109:
2076:
2072:
2062:
2021:
2017:
2007:
1974:
1970:
1924:
1920:
1910:
1893:
1889:
1879:
1854:
1850:
1840:
1805:
1802:Microbiology
1801:
1755:
1751:
1741:
1690:
1686:
1652:
1648:
1638:
1593:
1589:
1579:
1557:(1): 45–50.
1554:
1550:
1540:
1529:, retrieved
1507:
1477:
1473:
1463:
1452:, retrieved
1430:
1420:
1387:
1383:
1343:
1339:
1329:
1304:
1300:
1290:
1260:(1): 29–37.
1257:
1253:
1213:
1209:
1199:
1166:
1162:
1152:
1117:
1113:
1103:
1076:
1072:
1062:
1037:
1033:
1023:
1006:
1002:
992:
980:. Retrieved
976:
966:
955:, retrieved
948:
942:
931:, retrieved
909:
899:
887:. Retrieved
883:
874:
857:
853:
801:
797:
767:
763:
707:
704:
693:
683:during DszB
670:
642:
637:
630:subculturing
622:
605:
595:
584:
567:nicotinamide
548:
538:attack to SO
528:
516:
494:
475:
428:
396:
371:
355:
347:
331:
321:
307:
300:
299:and further
297:NAD cofactor
288:
276:
272:
267:
264:
228:
200:heterocycles
197:
174:
154:
123:
103:fossil fuels
68:
45:
19:
18:
2126:: 385–390.
1531:December 8,
1454:December 8,
1094:10261/21476
982:December 7,
977:www.epa.gov
957:December 7,
933:December 7,
889:December 7,
860:: 163–180.
681:active site
643:The strong
638:Rhodococcus
615:transformed
607:Rhodococcus
542:forming HSO
441:(DBT) into
419:deasphalted
380:desulfinase
374:genes (the
304:oxygenation
254:fractions.
164:metric tons
99:noble metal
2364:Categories
740:References
677:bottleneck
463:byproducts
384:chromosome
312:hydrolysis
218:, product
193:thiophenes
126:combustion
87:refineries
83:acid rains
79:atmosphere
42:Background
2295:1573-6776
2240:0916-8451
2195:167219836
2179:2161-5063
2140:0016-2361
2093:0958-1669
2046:1089-5639
1999:225512533
1991:2155-5435
1949:105202414
1941:2155-5435
1824:1350-0872
1715:0099-2240
1612:1660-4601
1571:0002-1369
1412:229112004
1404:1463-9262
1282:110105610
1274:1618-954X
1232:0888-5885
1191:247972735
1183:0887-0624
1136:2190-5525
1054:0016-2361
818:1091-6466
661:wild-type
536:hydroxide
336:sulfoxide
208:cofactors
146:oxidative
95:poisoning
91:corrosion
77:) to the
34:or their
28:crude oil
2350:28976031
2311:44991374
2303:20349330
2256:12721389
2248:17986771
2187:31132321
2101:16678400
2054:27128525
1871:10630342
1780:23160813
1772:10068795
1733:24096431
1630:19440284
1360:19819129
1321:16716940
1144:94952018
826:96330432
728:See also
710:sequence
657:activity
486:cofactor
386:encoded
316:pyruvate
111:jet fuel
56:hydrogen
2026:Bibcode
1832:9308179
1724:3837836
1695:Bibcode
1621:2672333
714:hydride
665:docking
619:plasmid
617:with a
611:strains
563:hydride
447:sulfite
411:bitumen
368:enzymes
364:sulfite
340:sulfone
240:sulfite
236:sulfide
204:enzymes
97:of the
48:element
36:enzymes
2375:Sulfur
2348:
2309:
2301:
2293:
2254:
2246:
2238:
2193:
2185:
2177:
2138:
2099:
2091:
2052:
2044:
1997:
1989:
1947:
1939:
1869:
1830:
1822:
1778:
1770:
1731:
1721:
1713:
1628:
1618:
1610:
1569:
1522:
1445:
1410:
1402:
1358:
1319:
1280:
1272:
1230:
1189:
1181:
1142:
1134:
1052:
924:
824:
816:
653:mutant
626:operon
490:oxygen
459:oxygen
388:enzyme
372:dszABC
354:and a
185:sulfur
177:sulfur
107:diesel
52:carbon
50:after
24:sulfur
2307:S2CID
2252:S2CID
2191:S2CID
1995:S2CID
1945:S2CID
1867:S2CID
1776:S2CID
1408:S2CID
1278:S2CID
1187:S2CID
1140:S2CID
822:S2CID
613:were
417:, or
109:, or
60:sweet
26:from
2346:PMID
2299:PMID
2291:ISSN
2244:PMID
2236:ISSN
2183:PMID
2175:ISSN
2136:ISSN
2120:Fuel
2097:PMID
2089:ISSN
2050:PMID
2042:ISSN
1987:ISSN
1937:ISSN
1890:Fuel
1828:PMID
1820:ISSN
1768:PMID
1729:PMID
1711:ISSN
1626:PMID
1608:ISSN
1567:ISSN
1533:2022
1520:ISBN
1456:2022
1443:ISBN
1400:ISSN
1356:PMID
1317:PMID
1270:ISSN
1228:ISSN
1179:ISSN
1132:ISSN
1050:ISSN
1034:Fuel
1003:Fuel
984:2022
959:2022
935:2022
922:ISBN
891:2022
814:ISSN
718:NADH
590:rate
585:The
559:NADH
451:NADH
445:and
362:and
356:iii)
338:and
310:the
301:iii)
291:the
271:and
64:sour
54:and
2338:doi
2283:doi
2226:doi
2167:doi
2128:doi
2124:112
2081:doi
2034:doi
2022:120
1979:doi
1929:doi
1898:doi
1859:doi
1810:doi
1806:143
1760:doi
1719:PMC
1703:doi
1657:doi
1616:PMC
1598:doi
1559:doi
1512:doi
1482:doi
1435:doi
1392:doi
1348:doi
1344:101
1309:doi
1305:101
1262:doi
1218:doi
1171:doi
1122:doi
1089:hdl
1081:doi
1042:doi
1011:doi
914:doi
862:doi
858:110
806:doi
772:doi
722:FAD
720:to
649:HBP
634:DBT
623:dsz
497:cat
484:as
478:DBT
348:ii)
308:iv)
289:ii)
283:by
238:or
134:ppm
73:(SO
62:or
2366::
2344:.
2334:23
2332:.
2328:.
2305:.
2297:.
2289:.
2279:32
2277:.
2273:.
2250:.
2242:.
2234:.
2222:71
2220:.
2216:.
2189:.
2181:.
2173:.
2161:.
2157:.
2134:.
2122:.
2118:.
2095:.
2087:.
2077:17
2071:.
2048:.
2040:.
2032:.
2020:.
2016:.
1993:.
1985:.
1975:10
1973:.
1969:.
1957:^
1943:.
1935:.
1923:.
1919:.
1894:76
1892:.
1888:.
1865:.
1855:23
1853:.
1849:.
1826:.
1818:.
1804:.
1800:.
1788:^
1774:.
1766:.
1756:74
1754:.
1750:.
1727:.
1717:.
1709:.
1701:.
1691:79
1689:.
1685:.
1669:^
1653:40
1651:.
1647:.
1624:.
1614:.
1606:.
1592:.
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