View : 32 Download: 0

Chemoenzymatic Synthesis of Glycosylated Macrolactam Analogues of the Macrolide Antibiotic YC-17

Title
Chemoenzymatic Synthesis of Glycosylated Macrolactam Analogues of the Macrolide Antibiotic YC-17
Authors
Shinde, Pramod B.Oh, Hong-SeChoi, HyeminRathwell, KrisBan, Yeon HeeKim, Eun JiYang, InhoLee, Dong GunSherman, David H.Kang, Han-YoungYoon, Yeo Joon
Ewha Authors
윤여준Pramod B. Shinde
SCOPUS Author ID
윤여준scopus
Issue Date
2015
Journal Title
ADVANCED SYNTHESIS & CATALYSIS
ISSN
1615-4150JCR Link1615-4169JCR Link
Citation
vol. 357, no. 12, pp. 2697 - 2711
Keywords
antibacterial activityglycosyltransferasemacrolide glycosidesStreptomyces venezuelaeYC-17
Publisher
WILEY-V C H VERLAG GMBH
Indexed
SCI; SCIE; SCOPUS WOS scopus
Abstract
YC-17 is a 12-membered ring macrolide antibiotic produced from Streptomyces venezuelae ATCC 15439 and is composed of the polyketide macrolactone 10-deoxymethynolide appended with D-desosamine. In order to develop structurally diverse macrolactam analogues of YC-17 with improved therapeutic potential, a combined approach involving chemical synthesis and engineered cell-based biotransformation was employed. Eight new antibacterial macrolactam analogues of YC-17 were generated by supplying a novel chemically synthesized macrolactam aglycone to S. venezuelae mutants harboring plasmids capable of synthesizing several unnatural sugars for subsequent glycosylation. Some YC-17 macrolactam analogues were active against erythromycin-resistant bacterial pathogens and displayed improved metabolic stability in vitro. The enhanced therapeutic potential demonstrated by these glycosylated macrolactam analogues reveals the unique potential of chemoenzymatic synthesis in antibiotic drug discovery and development.
DOI
10.1002/adsc.201500250
Appears in Collections:
자연과학대학 > 화학·나노과학전공 > Journal papers
Files in This Item:
There are no files associated with this item.
Export
RIS (EndNote)
XLS (Excel)
XML


qrcode

Items in DSpace are protected by copyright, with all rights reserved, unless otherwise indicated.

BROWSE