Open AccessA New Synthetic Approach toward Bacterial Transglycosylase Substrates, Lipid II and Lipid IV
Author(s) -
HaoWei Shih,
KuoTing Chen,
Ting-Jen Rachel Cheng,
ChiHuey Wong,
WeiChieh Cheng
Publication year - 2011
Publication title -
organic letters
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.94
H-Index - 239
eISSN - 1523-7060
pISSN - 1523-7052
DOI - 10.1021/ol201806d
Subject(s) - chemistry , lipid ii , lipid a , biochemistry , disaccharide , enzyme , pyrophosphate , oligopeptide , reactivity (psychology) , stereochemistry , lipid metabolism , biosynthesis , bacteria , peptide , medicine , alternative medicine , pathology , biology , genetics
A new synthetic approach toward the bacterial transglycosylase substrates, Lipid II (1) and Lipid IV (2), is described. The key disaccharide was synthesized using the concept of relative reactivity value (RRV) and elaborated to Lipid II and Lipid IV by conjugation with the appropriate oligopeptides and pyrophosphate lipids. Interestingly, the results from our HPLC-based functional TGase assay suggested Lipid IV has a higher affinity for the enzyme than Lipid II.
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