425:(GGDP) and an N-terminal terpene cyclase domain where GGDP gets cyclized and turns into fusicocca-2,10(14)-diene. It is also reported in this study that a 2-oxoglutarate-dependent dioxygenase-like gene, a cytochrome P450 monooxygenase-like gene, a short-chain dehydrogenase/reductase-like gene, and an α-mannosidase-like gene at the 3’ location downstream of PaFS which are responsible for converting fusicocca-2,10(14)-diene into fusicoccin. Two enzymes, one dioxygenase and PAPT, are in charge of catalyzing a hydroxylation at the 3-position of fusicocca-2,10(14)-diene-8β,16-diol and prenylation of the hydroxyl group of
433:
189:
90:
24:
212:
InChI=1S/C36H56O12/c1-10-35(6,7)45-17-26-30(41)33(46-21(5)38)31(42)34(47-26)48-32-28-24(18(2)15-44-20(4)37)13-27(39)36(28,8)14-25-22(16-43-9)11-12-23(25)19(3)29(32)40/h10,14,18-19,22-23,26-27,29-34,39-42H,1,11-13,15-17H2,2-9H3/b25-14-/t18-,19-,22-,23+,26-,27+,29-,30-,31-,32-,33+,34-,36+/m1/s1
222:
InChI=1/C36H56O12/c1-10-35(6,7)45-17-26-30(41)33(46-21(5)38)31(42)34(47-26)48-32-28-24(18(2)15-44-20(4)37)13-27(39)36(28,8)14-25-22(16-43-9)11-12-23(25)19(3)29(32)40/h10,14,18-19,22-23,26-27,29-34,39-42H,1,11-13,15-17H2,2-9H3/b25-14-/t18-,19-,22-,23+,26-,27+,29-,30-,31-,32-,33+,34-,36+/m1/s1
625:
Noike M, Liu C, Ono Y, Hamano Y, Toyomasu T, Sassa T, Kato N, Dairi T (2012). "An enzyme catalyzing o-prenylation of the glucose moiety of fusicoccin A, a diterpene glucoside produced by the fungus phopopsis amygdali".
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Ono Y, Minami A, Noike M, Higuchi Y, Toyoasu T, Sassa T, Kato N, Dairi T (2011). "Dioxygenases, keyenzymes to determine the aglycon structures of fusicoccin and brassicicene, diterpene compounds produced by fungi".
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Fusicoccin is a member of a diterpenoid class which shares a 5-8-5 ring structure and is called fusicoccane. In fungi, fusicoccin is biosynthesized via
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44:)-2-oxy}-1,5-dihydroxy-9-(methoxymethyl)-6,10a-dimethyl-1,2,4,5,6,6a,7,8,9,10a-decahydrodicyclopentaannulen-3-yl]propyl acetate
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310:
167:
422:
675:
414:
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de Boer AH, de Vries-van
Leeuwen IJ (2012). "Fusicoccanes: diterpenes with surprising biological functions".
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36:
421:(IPP). PaFS has two domains, a C-terminal prenyltransferase domain which converts isoprene units into
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Toyomasu T, Tsukahara M, Kaneko A, Niida R, Mitsuhashi W, Dairi T, Kato N, Sassa T (2007).
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Ballio, A.; Chain, E. B.; De Leo, P.; Erlanger, B. F.; Mauri, M.; Tonolo, A. (1964).
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O=C(OC(\C3=C2/(O1O((O)(OC(=O)C)1O)COC(\C=C)(C)C)(O)(C)4C(=C/2(C)(O)C3)\(COC)CC4)C)C
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532:"Fusicoccins are biosynthesized by an unusual chimera diterpene synthase in fungi"
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Except where otherwise noted, data are given for materials in their
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456:"Fusicoccin: a new wilting toxin produced by Fusicoccum amygdali"
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Fusicoccin was and is extensively used in research regarding the
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to irreversibly open, which brings about the death of the plant.
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Fusicoccins are diterpenoid glycosides produced by the fungus
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365:. It stimulates a quick acidification of the plant
409:fusicoccadiene synthase (PaFS) from universal C5
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380:rings and another ring which contains an
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215:Key: KXTYBXCEQOANSX-WYKQKOHHSA-N
7:
436:Biosynthesis Pathway of Fusicoccins
225:Key: KXTYBXCEQOANSX-WYKQKOHHBW
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14:
376:Fusicoccins contains three fused
273:
22:
429:in fusicoccin P, respectively.
333:. It has detrimental effect on
307:(at 25 °C , 100 kPa).
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267:
1:
509:10.1016/j.tplants.2012.02.007
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423:geranylgeranyl diphosphate
415:dimethylallyl diphosphate
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35:
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557:10.1073/pnas.0608426104
497:Trends in Plant Science
419:isopentenyl diphosphate
640:10.1002/cbic.201100725
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686:Diterpene glycosides
397:and its mechanisms.
548:2007PNAS..104.3084T
472:1964Natur.203..297B
347:Fusicoccum amygdali
297: g·mol
18:
438:
407:Phomopsis amygdali
387:and five carbons.
369:; this causes the
311:Infobox references
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604:10.1021/ja107785u
337:and causes their
327:organic compounds
319:Chemical compound
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168:CompTox Dashboard
91:Interactive image
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676:Plant physiology
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598:(8): 2548–2555.
592:J. Am. Chem. Soc
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329:produced by a
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466:(4942): 297.
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17:Fusicoccin A
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417:(DMAPP) and
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50:Identifiers
41:
628:ChemBioChem
323:Fusicoccins
255:Properties
670:Categories
441:References
354:of mainly
290:Molar mass
102:ChemSpider
78:3D model (
67:20108-30-9
57:CAS Number
37:IUPAC name
367:cell wall
656:36028964
648:22287087
612:21299202
576:17360612
517:22465041
411:isoprene
352:parasite
122:DrugBank
567:1805559
544:Bibcode
468:Bibcode
427:glucose
371:stomata
295:680.832
143:PubChem
131:DB01780
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610:
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460:Nature
413:units
382:oxygen
378:carbon
356:almond
335:plants
331:fungus
239:SMILES
156:447573
111:394625
31:Names
652:S2CID
395:auxin
363:trees
360:peach
339:death
204:InChI
80:JSmol
644:PMID
608:PMID
572:PMID
536:PNAS
513:PMID
385:atom
358:and
325:are
636:doi
600:doi
596:133
562:PMC
552:doi
540:104
505:doi
476:doi
464:203
173:EPA
146:CID
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280:O
274:H
268:C
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171:(
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42:S
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