212:
471:
30:
454:
domain PltA then dichlorinates the pyrrole moiety first at position 5 and then at position 4 in a FADH2 dependent manner. The dichloropyrroyl residue is then transferred to the type I PKS PltB and PltC, however, the mechanism of transfer is unknown. The addition of 3 malonyl-CoA
445:
domain PltF. With prolyl-AMP still in the active site, the active form of the peptidyl carrier protein PltL binds to PltF. Then PltF catalyzes the aminoacylation of PltL by attaching L-proline to the thiol of the 4’phosphopantetheine arm of PltL. Next, the
671:
Nowak-Thompson B, Gould SJ, Loper JE (December 1997). "Identification and sequence analysis of the genes encoding a polyketide synthase required for pyoluteorin biosynthesis in
Pseudomonas fluorescens Pf-5".
584:
Howell CR (January 16, 1980). "Suppression of
Pythium ultimum-induced damping-off of cotton seedlings by pseudomonas fluorescens and its antibiotic, pyoluteorin".
288:
875:
302:
414:
640:"Biosynthesis of Pyoluteorin: A Mixed Polyketide-Tricarboxylic Acid Cycle Origin Demonstrated by [l,2-13C2]Acetate Incorporation"
322:
45:
131:
191:
803:"Dichlorination of a pyrrolyl-S-carrier protein by FADH2-dependent halogenase PltA during pyoluteorin biosynthesis"
798:
758:"Conversion of L-proline to pyrrolyl-2-carboxyl-S-PCP during undecylprodigiosin and pyoluteorin biosynthesis"
373:
180:
870:
865:
814:
491:
Gross H, Loper JE (November 2009). "Genomics of secondary metabolite production by
Pseudomonas spp".
410:
that causes a global loss in agriculture. Currently, pyoluteorin derivatives are being studied as an
361:
207:
368:
66:
434:
470:
709:"Characterization of the pyoluteorin biosynthetic gene cluster of Pseudomonas fluorescens Pf-5"
160:
880:
842:
779:
738:
689:
508:
832:
822:
769:
728:
720:
681:
651:
620:
593:
566:
535:
500:
377:
358:
228:
140:
120:
75:
611:
Doi K (October 2014). "Characterization of pyoluteorin derivatives as Mcl-1 antagonists".
460:
402:
211:
437:
is derived from a type II NRPS. Pyoluteorin biosynthesis begins with the activation of L-
818:
837:
802:
407:
774:
757:
685:
859:
733:
708:
447:
442:
330:
InChI=InChI=1S/C11H7Cl2NO3/c12-5-4-6(14-11(5)13)10(17)9-7(15)2-1-3-8(9)16/h1-4,14-16H
724:
464:
451:
354:
624:
553:
Maurhofer M (September 10, 1991). "Influence of
Enhanced Antibiotic Production in
100:
807:
Proceedings of the
National Academy of Sciences of the United States of America
430:
350:
264:
111:
827:
21:
846:
783:
742:
656:
639:
512:
693:
597:
570:
389:
385:
381:
539:
450:
PltE desaturates the prolyl moiety on PltL to create pyrrolyl-PltL. The
29:
456:
438:
86:
707:
Nowak-Thompson B, Chaney N, Wing JS, Gould SJ, Loper JE (April 1999).
504:
418:
393:
364:
171:
400:. Pyoluteorin is most notable for its toxicity against the oomycete
469:
397:
287:
278:
151:
429:
Pyoluteorin is synthesized from an NRPS/PKS hybrid pathway. The
411:
371:(PKS) pathway. Pyoluteorin was first isolated in the 1950s from
526:
Takeda R (1958). "Structure of a new antibiotic, pyoluteorin".
433:
ring is derived from a type I PKS while the dichloropyrrole
196:
474:
Pyoluteorin biosynthesis. Asterisk denotes inactive domain.
276:
263:
227:
222:
190:
170:
150:
130:
110:
85:
65:
36:
557:Strain CHA0 on its Disease Suppressive Capacity".
756:Thomas MG, Burkart MD, Walsh CT (February 2002).
99:
74:
8:
57:-pyrrol-2-yl)-(2,6-dihydroxyphenyl)methanone
20:
801:, Kelleher NL, Walsh CT (September 2005).
210:
119:
836:
826:
773:
732:
655:
310:C1=CC(=C(C(=C1)O)C(=O)C2=CC(=C(N2)Cl)Cl)O
139:
528:Journal of the American Chemical Society
483:
327:
307:
206:
50:
380:T359 and IFO 3455 and was found to be
19:
179:
159:
7:
876:Halogen-containing natural products
90:
14:
421:that have elevated Mcl-1 levels.
644:Zeitschrift für Naturforschung C
251:
245:
239:
28:
725:10.1128/JB.181.7.2166-2174.1999
638:Cuppels DA (January 15, 1986).
335:Key:JPGWTZORMBTNMF-UHFFFAOYSA-N
254:
233:
1:
775:10.1016/S1074-5521(02)00100-X
686:10.1016/S0378-1119(97)00501-5
625:10.1158/1538-7445.AM2014-1805
897:
223:Chemical and physical data
318:
298:
41:
27:
467:PltG gives pyoluteorin.
828:10.1073/pnas.0506964102
762:Chemistry & Biology
713:Journal of Bacteriology
555:Pseudomonas fluorescens
493:Natural Product Reports
797:Dorrestein PC, Yeh E,
657:10.1515/znc-1986-5-607
475:
396:, and against certain
374:Pseudomonas aeruginosa
473:
463:, and release by the
441:to prolyl-AMP by the
598:10.1094/Phyto-70-712
571:10.1094/Phyto-82-190
362:nonribosomal peptide
819:2005PNAS..10213843D
799:Garneau-Tsodikova S
540:10.1021/ja01550a093
417:in order to target
369:polyketide synthase
24:
476:
534:(17): 4749–4750.
343:
342:
289:Interactive image
192:CompTox Dashboard
16:Chemical compound
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851:
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650:(5–6): 532–536.
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505:10.1039/b817075b
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813:(39): 13843–8.
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613:Cancer Research
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499:(11): 1408–46.
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403:Pythium ultimum
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53:(4,5-Dichloro-1
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789:
748:
719:(7): 2166–74.
699:
680:(1–2): 17–24.
663:
630:
603:
592:(8): 712–715.
586:Phytopathology
576:
565:(2): 190–195.
559:Phytopathology
545:
518:
482:
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426:
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408:plant pathogen
355:biosynthesized
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208:DTXSID30180384
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768:(2): 171–84.
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448:dehydrogenase
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406:, which is a
405:
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399:
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349:is a natural
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181:ChEMBL2286204
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871:Biosynthesis
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806:
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751:
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633:
619:(19): 1805.
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589:
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579:
562:
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548:
531:
527:
521:
496:
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465:thioesterase
452:halogenation
428:
425:Biosynthesis
401:
372:
346:
345:
161:CHEBI:156453
54:
866:Antibiotics
461:cyclization
443:adenylation
367:(NRPS) and
347:Pyoluteorin
272: g·mol
37:Identifiers
22:Pyoluteorin
860:Categories
479:References
431:resorcinol
415:antagonist
365:synthetase
351:antibiotic
277:3D model (
265:Molar mass
141:3YM4R964TU
112:ChemSpider
76:25683-07-2
67:CAS Number
46:IUPAC name
386:oomycetes
881:Pyrroles
847:16162666
784:11880032
743:10094695
513:19844639
457:monomers
390:bacteria
384:against
353:that is
838:1236592
815:Bibcode
694:9434161
439:proline
419:cancers
378:strains
357:from a
229:Formula
87:PubChem
845:
835:
782:
741:
731:
692:
511:
435:moiety
398:plants
359:hybrid
303:SMILES
270:272.08
172:ChEMBL
734:93630
412:Mcl-1
394:fungi
382:toxic
323:InChI
279:JSmol
152:ChEBI
121:30629
101:33137
843:PMID
780:PMID
739:PMID
690:PMID
674:Gene
509:PMID
132:UNII
833:PMC
823:doi
811:102
770:doi
729:PMC
721:doi
717:181
682:doi
678:204
652:doi
621:doi
594:doi
567:doi
536:doi
501:doi
197:EPA
91:CID
862::
841:.
831:.
821:.
809:.
805:.
778:.
764:.
760:.
737:.
727:.
715:.
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688:.
676:.
648:41
646:.
642:.
617:74
615:.
590:70
588:.
563:82
561:.
532:80
530:.
507:.
497:26
495:.
459:,
392:,
388:,
246:Cl
237:11
849:.
825::
817::
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772::
766:9
745:.
723::
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684::
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654::
627:.
623::
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596::
573:.
569::
542:.
538::
515:.
503::
281:)
258:3
255:O
252:N
249:2
243:7
240:H
234:C
199:)
195:(
55:H
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