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Dissection of Two Acyl‐Transfer Reactions Centered on Acyl‐S‐Carrier Protein Intermediates for Incorporating 5‐Chloro‐6‐methyl‐ O ‐methylsalicyclic Acid into Chlorothricin
Author(s) -
He QingLi,
Jia XinYing,
Tang ManCheng,
Tian ZhenHua,
Tang GongLi,
Liu Wen
Publication year - 2009
Publication title -
chembiochem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.05
H-Index - 126
eISSN - 1439-7633
pISSN - 1439-4227
DOI - 10.1002/cbic.200800714
Subject(s) - chemistry , residue (chemistry) , nucleophile , acyl group , acyl carrier protein , acylation , acyltransferase , stereochemistry , side chain , mutant , thioester , biochemistry , enzyme , biosynthesis , organic chemistry , group (periodic table) , gene , catalysis , polymer
Making the microbes work for us : An acyl‐carrier‐protein‐centered strategy that involves two distinct acyl‐transfer steps for generation and regiospecific attachment of the 5‐chloro‐6‐methyl‐ O ‐methylsalicyl group onto the C3′ position of D ‐olivose was elucidated in the biosynthetic pathway of chlorothricin. Identification of the mutant of the acyltransferase‐associated intermediate validated the critical role of the highly conserved Cys residue, which channels the acyl transfer by using its thiolate side chain as a nucleophile in a two‐step process.