Browse history interactively

Page 1

Page 1Revision 1

Page 2

Page 2Revision 2

← Previous editContent deleted Content addedVisualWikitext

Revision as of 21:45, 18 July 2011 editCheMoBot (talk | contribs)Bots141,565 edits Updating {{chembox}} (changes to watched fields - added verified revid - updated 'UNII_Ref', 'ChemSpiderID_Ref', 'StdInChI_Ref', 'StdInChIKey_Ref', 'ChEMBL_Ref', 'KEGG_Ref') per [[Misplaced Pages:WikiProject Chemicals/Chembox validation|Chem/Drugbox valida← Previous edit		Latest revision as of 04:19, 25 January 2025 edit undoMfernflower (talk | contribs)Extended confirmed users7,998 editsNo edit summaryTags: Mobile edit Mobile web edit Advanced mobile edit
(29 intermediate revisions by 21 users not shown)
Line 1:		Line 1:
	{{Orphan|date=March 2011}}
	{{chembox		{{chembox
	| Watchedfields = changed		| Watchedfields = changed
	| verifiedrevid = 431734115		| verifiedrevid = 440195685
	| ImageFile = codinaeopsin.png		| ImageFile = Codinaeopsin.svg
	| ImageSize =		| ImageSize =
	| IUPACName = 5-((1''H''-indol-3-yl)methyl)-3-((1''R'',2''R'',4a''S'',6''R'',8''S'',8a''S'')-2-((''E'')-but-2-en-2-yl)-4a,6,8-trimethyl-1,2,4a,5,6,7,8,8a-octahydronaphthalene-1-carbonyl)-5-hydroxy-1''H''-pyrrol-2(5'''H'')-one		| IUPACName = 5-((1''H''-indol-3-yl)methyl)-3-((1''R'',2''R'',4a''S'',6''R'',8''S'',8a''S'')-2-((''E'')-but-2-en-2-yl)-4a,6,8-trimethyl-1,2,4a,5,6,7,8,8a-octahydronaphthalene-1-carbonyl)-5-hydroxy-1''H''-pyrrol-2(5'''H'')-one
	| OtherNames =		| OtherNames =
	| Section1 = {{Chembox Identifiers		|Section1={{Chembox Identifiers
	| CASNo =		| CASNo = 1055291-88-7
	| PubChem =		| ChEBI = 222711
	| SMILES =		| PubChem = 102412273
			| ChemSpiderID = 129562509
			| SMILES = C/C=C(\C)/1(2(C(C2(C=C1C)C)C)C)C(=O)C3=CC(NC3=O)(CC4=CNC5=CC=CC=C54)O
			| StdInChI = 1S/C32H40N2O3/c1-7-19(3)26-21(5)14-31(6)13-18(2)12-20(4)28(31)27(26)29(35)24-16-32(37,34-30(24)36)15-22-17-33-25-11-9-8-10-23(22)25/h7-11,14,16-18,20,26-28,33,37H,12-13,15H2,1-6H3,(H,34,36)/b19-7+/t18-,20+,26-,27-,28+,31+,32?/m1/s1
			| StdInChIKey = FFIWOIAVVDGNHZ-ZQXRKGDHSA-N
	}}		}}
	| Section2 = {{Chembox Properties		|Section2={{Chembox Properties
	| C=31|H=38|N=2|O=3		| C=32 | H=40 | N=2 | O=3
	| Appearance =		| Appearance =
	| Density =		| Density =
	| MeltingPtC =		| MeltingPtC =
	| BoilingPt =		| BoilingPt =
	| Solubility =		| Solubility =
	}}		}}
	| Section3 = {{Chembox Hazards		|Section3={{Chembox Hazards
	| MainHazards =		| MainHazards =
	| FlashPt =		| FlashPt =
	| Autoignition =		| AutoignitionPt =
	}}		}}
	}}		}}
	'''Codinaeopsin''' is an ] isolated from a ] isolate found in ]s (''Vochysia guatemalensis'') in ]. It is reported to have bioactivity against '']'' with an IC<sub>50</sub> = 2.3&nbsp;µg/mL (4.7&nbsp;µM). Pure codinaeopsin was reported to be isolated with a total yield of 18&nbsp;mg/mL from cultured fungus.<ref name=Isolation>{{cite journal|last=Kotinik|first=Renee|coauthors=Clardy, Jon|title=Codinaeopsin, an Antimalarial Fungal Polyketide|journal=Org. Lett.|year=2008|volume=10|issue=18|pages=4149-4151|doi=10.1021/ol801726k}}</ref> The ] of codinaeopsin is manufactured by a ]- ] (PKS-NRPS) hybrid.		'''Codinaeopsin''' is an ] alkaloid isolated from a endophytic mold found in '']'' trees in ]. It is reported to have bioactivity against '']'' with an IC<sub>50</sub> = 2.3&nbsp;μg/mL (4.7&nbsp;μM). Pure codinaeopsin was reported to be isolated with a total yield of 18&nbsp;mg/mL from cultured fungus.<ref name="Isolation">{{cite journal|last=Kontnik|first=Renee|year=2008|title=Codinaeopsin, an Antimalarial Fungal Polyketide|journal=Org. Lett.|volume=10|issue=18|pages=4149–4151|doi=10.1021/ol801726k|author2=Clardy, Jon|pmid=18698786|authorlink2=Jon Clardy|pmc=2626159}}</ref> The ] of codinaeopsin involves a ]-] (PKS-NRPS) hybrid.
	==Biosynthesis==		==Biosynthesis==
	===Formation of linear polyketide===		===Formation of linear polyketide===
	The first step of the biosynthesis of codinaeopsin involves the assembly of the a linear ] by use of seven modules and incorporation of six ]s and one ] by ] (type I PKSs).<ref name=Isolation>{{cite journal|last=Kotinik|first=Renee|coauthors=Clardy, Jon|title=Codinaeopsin, an Antimalarial Fungal Polyketide|journal=Org. Lett.|year=2008|volume=10|issue=18|pages=4149-4151|doi=10.1021/ol801726k}}</ref>		The first step of the biosynthesis of codinaeopsin involves the assembly of the a linear ] by use of seven modules and incorporation of six ]s and one ] by ] (type I PKSs).<ref name=Isolation/>
	]		]
	<br />
	===Formation of tetramic acid (2,4-pyrrolidindione)===		===Formation of tetramic acid (2,4-pyrrolidinone)===
	] is introduced by a ] (NRPS) module and results in the central ] tetramic acid (2,4-pyrrolidindione). The formal oxidation-reduction is found to be achieved by a series of tautomeric shifts involving ] and ] intermediates in the ring and consistent by discovery both C-2’ ]s.<ref name=Isolation>{{cite journal|last=Kotinik|first=Renee|coauthors=Clardy, Jon|title=Codinaeopsin, an Antimalarial Fungal Polyketide|journal=Org. Lett.|year=2008|volume=10|issue=18|pages=4149-4151|doi=10.1021/ol801726k}}</ref>		] is introduced by a ] (NRPS) module and results in the central ] tetramic acid (2,4-pyrrolidinone). The formal oxidation-reduction is found to be achieved by a series of tautomeric shifts involving ] and ] intermediates in the ring and consistent by discovery both C-2’ ]s.<ref name=Isolation/>
	===Cyclization of PKS-assembled unit===		===Cyclization of PKS-assembled unit===
	The PKS unit is hypothesized to cyclize by a ]-like addition similar to other ] such as ] and solanapyrone.<ref>{{cite journal|last=Auclair|first=K.|coauthors=Sutherland, A.; Kennedy, J.; Witter, D. J.; Van den Heever, J. P.; Hutchinson, C. R.; Vederas, J. C.|journal=J. Chem. Soc.|year=2000|volume=122|pages=11519|doi=10.1021/ja003216+}}</ref>		The PKS unit is hypothesized to cyclize by a ]-like addition similar to other ] such as ] and solanapyrone.<ref name="AuclairSutherland2000">{{cite journal|last1=Auclair|first1=Karine|author-link1=Karine Auclair|last2=Sutherland|first2=Andrew|last3=Kennedy|first3=Jonathan|last4=Witter|first4=David J.|last5=Van den Heever|first5=Johan P.|last6=Hutchinson|first6=C. Richard|last7=Vederas|first7=John C.|title=Lovastatin Nonaketide Synthase Catalyzes an Intramolecular Diels−Alder Reaction of a Substrate Analogue|journal=Journal of the American Chemical Society|volume=122|issue=46|year=2000|pages=11519–11520|issn=0002-7863|doi=10.1021/ja003216+|bibcode=2000JAChS.12211519A }}</ref>
	]		]
	==References==		== References ==
	{{reflist}}		{{reflist}}
	]
	]		]
	]