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Assembly of dimeric variants of coumermycins by tandem action of the four biosynthetic enzymes CouL, CouM, CouP, and NovN.

Abstract：

:Coumermycin A(1) is a member of the aminocoumarin family of antibiotics. Unlike its structural relatives, novobiocin and clorobiocin, coumermycin A(1) is a dimer built on a 3-methyl-2,4-dicarboxypyrrole scaffold and bears two decorated noviose sugar components which are the putative target binding motifs for DNA gyrase. Starting with this scaffold, we have utilized the ligase CouL for mono- and bisamide formation with aminocoumarins to provide substrates for the glycosyltransferase CouM. CouM was subsequently shown to catalyze mono- and bisnoviosylation of the resulting CouL products. CouP was shown to possess 4'-O-methyltransferase activity on products from tandem CouL, CouM assays. A fourth enzyme, NovN, the 3'-O-carbamoyltransferase from the novobiocin operon, was then able to carbamoylate either or both arms of the CouP product. The tandem action of CouL, CouM, CouP, and NovN thus generates a biscarbamoyl analogue of the pseudodimer coumermycin A(1). Starting from alternative dicarboxy scaffolds, these four enzymes can be utilized in tandem to create additional variants of dimeric aminocoumarin antibiotics.

journal_name

Biochemistry

journal_title

Biochemistry

authors

Freel Meyers CL,Oberthür M,Heide L,Kahne D,Walsh CT

doi

10.1021/bi048457z

subject

Has Abstract

pub_date

2004-11-30 00:00:00

pages

15022-36

issue

47

eissn

0006-2960

issn

1520-4995

journal_volume

43

pub_type

杂志文章

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