470456-68-9

Upstream product

• 135197-83-0 phenyl-3,4-O-diacetyl-2,6-dideoxy-1-thio-α-L-galactopyranoside 
• 167012-06-8 phenyl 3-O-benzoyl-2-deoxy-1-thio-α-L-fucopyranoside 
• 167012-93-3 phenyl 2-deoxy-1-thio-α-L-fucopyranoside 
• 108-24-7 acetic anhydride 
• 4551-15-9 phenylthiotrimethylsilane 

Relevant academic research and scientific papers

A systematic investigation of the synthetic utility of glycopeptide glycosyltransferases

Glycosyltransferases involved in the biosynthesis of bacterial secondary metabolites may be useful for the generation of sugar-modified analogues of bioactive natural products. Some glycosyltransferases have relaxed substrate specificity, and it has been assumed that promiscuity is a feature of the class. As part of a program to explore the synthetic utility of these enzymes, we have analyzed the substrate selectivity of glycosyltransferases that attach similar 2-deoxy-L-sugars to glycopeptide aglycons of the vancomycin-type, using purified enzymes and chemically synthesized TDP β-2-deoxy-L-sugar analogues. We show that while some of these glycopeptide glycosyltransferases are promiscuous, others tolerate only minor modifications in the substrates they will handle. For example, the glycosyltransferases GtfC and GtfD, which transfer 4-epi-L-vancosamine and L-vancosamine to C-2 of the glucose unit of vancomycin pseudoaglycon and chloroorienticin B, respectively, show moderately relaxed donor substrate specificities for the glycosylation of their natural aglycons. In contrast, GtfA, a transferase attaching 4-epi-L-vancosamine to a benzylic position, only utilizes donors that are closely related to its natural TDP sugar substrate. Our data also show that the spectrum of donors utilized by a given enzyme can depend on whether the natural acceptor or an analogue is used, and that GtfD is the most versatile enzyme for the synthesis of vancomycin analogues.

Towards the synthesis of aureolic acid analogue conjugates: Synthesis and glycosidation reactions of 3-o-acetyl-4-azido-2,4,6-trideoxy-L-glucopyranose derivatives

A stereoselective synthesis of 3-O-acetyl-4-azido-glucopyranose (6) is described. The derived anomeric acetate (13), and especially the thioglycoside (14), are demonstrated to be good donors for synthesis of α-glycosides of (6). Donor (14) was used in the