The gene cluster responsible for the biosynthesis of Pseurotin A was predicted by deletion and overexpression of polyketide synthasenonribosomal peptide synthetase hybrid enzyme gene, PsoA.[2] While it is unknown how the azaspirocyclic core of the pseurotin family of natural products is made, the post polyketide synthase modifications are known. In-vivo and in-vitro studies showed the unique mechanism involved in the modification enzymes PsoC, PsoD, PsoE, and PsoF. PsoD codes for a cytochrome P450, which is responsible for oxidizing the benzyl carbon (C17) to the conjugated ketone. PsoC codes for a methyltransferase, which methylates the tertiary alcohol closest to the benzoyl moiety on C8. PsoE is predicted to be a glutathione S-transferase gene, and isomerizes the C=C bond furthest down the tail from the E stereoisomer to the Z stereoisomer. PsoF is unique in that its gene is encoded separate from the pseurotin gene cluster and is responsible for the epoxidation of the trans double bond that remains in the tail. This epoxide is spontaneously hydrolyzed by either an SN2 mechanism to form pseurotin A, or by an SN2’ mechanism to form pseurotin D.[3]
^Martínez-Luis, S; Cherigo, L; Arnold, E; Spadafora, C; Gerwick, WH; Cubilla-Rios, L (2012). "Antiparasitic and anticancer constituents of the endophytic fungus Aspergillus sp. Strain F1544". Natural Product Communications. 7 (2): 165–8. doi:10.1177/1934578X1200700207. PMID 22474943. S2CID 41167561.
^Maiya, Shubha; Grundmann, Alexander; Li, Xiang; Li, Shu-Ming; Turner, Geoffrey (2007-09-24). "Identification of a Hybrid PKS/NRPS Required for Pseurotin A Biosynthesis in the Human PathogenAspergillus fumigatus". ChemBioChem. 8 (14): 1736–1743. doi:10.1002/cbic.200700202. ISSN 1439-4227. PMID 17722120. S2CID 9394131.
^Tsunematsu, Yuta; Fukutomi, Manami; Saruwatari, Takayoshi; Noguchi, Hiroshi; Hotta, Kinya; Tang, Yi; Watanabe, Kenji (2014-06-18). "Elucidation of Pseurotin Biosynthetic Pathway Points to Trans-ActingC-Methyltransferase: Generation of Chemical Diversity". Angewandte Chemie. 126 (32): 8615–8619. doi:10.1002/ange.201404804. ISSN 0044-8249. PMC4605568. PMID 24939566.
May 01, 2024
pseurotin, secondary, metabolite, aspergillus, names, preferred, iupac, name, benzoyl, dihydroxyhex, hydroxy, methoxy, methyl, azaspiro, dione, identifiers, number, 58523, model, jsmol, interactive, image, chebi, chebi, 64535, chembl, chembl253179, chemspider,. Pseurotin A is a secondary metabolite of Aspergillus 1 Pseurotin A Names Preferred IUPAC name 5S 8S 9R 8 Benzoyl 2 1S 2S 3Z 1 2 dihydroxyhex 3 en 1 yl 9 hydroxy 8 methoxy 3 methyl 1 oxa 7 azaspiro 4 4 non 2 ene 4 6 dione Identifiers CAS Number 58523 30 1 Y 3D model JSmol Interactive image ChEBI CHEBI 64535 ChEMBL ChEMBL253179 ChemSpider 8021336 PubChem CID 9845622 UNII H73C5W8FNE Y InChI InChI 1S C22H25NO8 c1 4 5 11 14 24 15 25 16 12 2 17 26 21 31 16 19 28 22 30 3 23 20 21 29 18 27 13 9 7 6 8 10 13 h5 11 14 15 19 24 25 28H 4H2 1 3H3 H 23 29 b11 5 t14 15 19 21 22 m0 s1Key SLYDIPAXCVVRNY UOWMTANKSA N SMILES CC C C C H C H C1 C C O C 2 O1 C H C NC2 O C O C3 CC CC C3 OC O C O O Properties Chemical formula C 22H 25N O 8 Molar mass 431 441 g mol 1 Except where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa Infobox referencesBiosynthesis editThe gene cluster responsible for the biosynthesis of Pseurotin A was predicted by deletion and overexpression of polyketide synthase nonribosomal peptide synthetase hybrid enzyme gene PsoA 2 While it is unknown how the azaspirocyclic core of the pseurotin family of natural products is made the post polyketide synthase modifications are known In vivo and in vitro studies showed the unique mechanism involved in the modification enzymes PsoC PsoD PsoE and PsoF PsoD codes for a cytochrome P450 which is responsible for oxidizing the benzyl carbon C17 to the conjugated ketone PsoC codes for a methyltransferase which methylates the tertiary alcohol closest to the benzoyl moiety on C8 PsoE is predicted to be a glutathione S transferase gene and isomerizes the C C bond furthest down the tail from the E stereoisomer to the Z stereoisomer PsoF is unique in that its gene is encoded separate from the pseurotin gene cluster and is responsible for the epoxidation of the trans double bond that remains in the tail This epoxide is spontaneously hydrolyzed by either an SN2 mechanism to form pseurotin A or by an SN2 mechanism to form pseurotin D 3 nbsp See also edit14 Norpseurotin AReferences edit Martinez Luis S Cherigo L Arnold E Spadafora C Gerwick WH Cubilla Rios L 2012 Antiparasitic and anticancer constituents of the endophytic fungus Aspergillus sp Strain F1544 Natural Product Communications 7 2 165 8 doi 10 1177 1934578X1200700207 PMID 22474943 S2CID 41167561 Maiya Shubha Grundmann Alexander Li Xiang Li Shu Ming Turner Geoffrey 2007 09 24 Identification of a Hybrid PKS NRPS Required for Pseurotin A Biosynthesis in the Human PathogenAspergillus fumigatus ChemBioChem 8 14 1736 1743 doi 10 1002 cbic 200700202 ISSN 1439 4227 PMID 17722120 S2CID 9394131 Tsunematsu Yuta Fukutomi Manami Saruwatari Takayoshi Noguchi Hiroshi Hotta Kinya Tang Yi Watanabe Kenji 2014 06 18 Elucidation of Pseurotin Biosynthetic Pathway Points to Trans ActingC Methyltransferase Generation of Chemical Diversity Angewandte Chemie 126 32 8615 8619 doi 10 1002 ange 201404804 ISSN 0044 8249 PMC 4605568 PMID 24939566 Retrieved from https en wikipedia org w index php title Pseurotin A amp oldid 1075845102, wikipedia, wiki, book, books, library,
