Isoprenoid-like alkylations in polyketide biosynthesis

被引:88
作者
Calderone, Christopher T. [1 ]
机构
[1] Harvard Univ, Sch Med, Dept Biol Chem & Mol Pharmacol, Boston, MA 02115 USA
关键词
D O I
10.1039/b807243d
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
Polyketides are secondary metabolites biosynthesized by the iterative Claisen condensation of malonate units. Despite utilizing only a small set of biochemical transformations, the polyketide biosynthetic machinery yields products Of Striking structural complexity and diversity. Recently, a new polyketicle alkylation pathway was characterized that allows access to "beta-branched" structures. This Highlight will describe this alkylation sequence, with special emphasis on its parallels to isoprenoid biosynthesis from primary metabolism and the scope of structures accessible via this pathway.
引用
收藏
页码:845 / 853
页数:9
相关论文
共 33 条
[1]   SEQUENCE AROUND THE 159-DEGREES REGION OF THE BACILLUS-SUBTILIS GENOME - THE PKSX LOCUS SPANS 33-CENTER-DOT-6 KB [J].
ALBERTINI, AM ;
CARAMORI, T ;
SCOFFONE, F ;
SCOTTI, C ;
GALIZZI, A .
MICROBIOLOGY-SGM, 1995, 141 :299-309
[2]   The identification of bacillaene, the product of the PksX megacomplex in Bacillus subtilis [J].
Butcher, Rebecca A. ;
Schroeder, Frank C. ;
Fischbach, Michael A. ;
Straightt, Paul D. ;
Kolter, Roberto ;
Walsh, Christopher T. ;
Clardy, Jon .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2007, 104 (05) :1506-1509
[3]   Incorporation of nonmethyl branches by lsoprenoid-like logic:: Multiple β-alkylation events in the biosynthesis of myxovirescin A1 [J].
Calderone, Christopher T. ;
Iwig, David F. ;
Dorrestein, Pieter C. ;
Kelleher, Neil L. ;
Walsh, Christopher T. .
CHEMISTRY & BIOLOGY, 2007, 14 (07) :835-846
[4]   Convergence of isoprene and polyketide biosynthetic machinery:: Isoprenyl-S-carrier proteins in the pksX pathway of Bacillus subtilis [J].
Calderone, Christopher T. ;
Kowtoniuk, Walter E. ;
Kelleher, Neil L. ;
Walsh, Christopher T. ;
Dorrestein, Pieter C. .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2006, 103 (24) :8977-8982
[5]   Hydroxymalonyl-acyl carrier protein (ACP) and aminomalonyl-ACP are two additional type I polyketide synthase extender units [J].
Chan, Yolande A. ;
Boyne, Michael T., II ;
Podevels, Angela M. ;
Klimowicz, Amy K. ;
Handelsman, Jo ;
Kelleher, Neil L. ;
Thomas, Michael G. .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2006, 103 (39) :14349-14354
[6]   Biosynthetic pathway and gene cluster analysis of curacin A, an antitubulin natural product from the tropical marine cyanobacterium Lyngbya majuscula [J].
Chang, ZX ;
Sitachitta, N ;
Rossi, JV ;
Roberts, MA ;
Flatt, PM ;
Jia, JY ;
Sherman, DH ;
Gerwick, WH .
JOURNAL OF NATURAL PRODUCTS, 2004, 67 (08) :1356-1367
[7]   MODULAR ORGANIZATION OF GENES REQUIRED FOR COMPLEX POLYKETIDE BIOSYNTHESIS [J].
DONADIO, S ;
STAVER, MJ ;
MCALPINE, JB ;
SWANSON, SJ ;
KATZ, L .
SCIENCE, 1991, 252 (5006) :675-679
[8]   Structure and biosynthesis of the jamaicamides, new mixed polyketide-peptide neurotoxins from the marine cyanobacterium Lyngbya majuscula [J].
Edwards, DJ ;
Marquez, BL ;
Nogle, LM ;
McPhail, K ;
Goeger, DE ;
Roberts, MA ;
Gerwick, WH .
CHEMISTRY & BIOLOGY, 2004, 11 (06) :817-833
[9]   Characterization of the mupirocin biosynthesis gene cluster from Pseudomonas fluorescens NCIMB 10586 [J].
El-Sayed, AK ;
Hothersall, J ;
Cooper, SM ;
Stephens, E ;
Simpson, TJ ;
Thomas, CM .
CHEMISTRY & BIOLOGY, 2003, 10 (05) :419-430
[10]   Assembly-line enzymology for polyketide and nonribosomal peptide antibiotics: Logic, machinery, and mechanisms [J].
Fischbach, Michael A. ;
Walsh, Christopher T. .
CHEMICAL REVIEWS, 2006, 106 (08) :3468-3496