312967-20-7Relevant academic research and scientific papers
Design and synthesis of novel cell wall inhibitors of Mycobacterium tuberculosis GlmM and GlmU
Li, Yongmeng,Zhou, Yan,Mac, Yufang,Li, Xuebing
, p. 1714 - 1720 (2011/12/02)
GlmM and GlmU are key enzymes in the biosynthesis of UDP-N-acetyl-D- glucosamine (UDP-GlcNAc), an essential precursor of peptidoglycan and the rhamnose-GlcNAc linker region in the mycobacterial cell wall. These enzymes are involved in the conversion of two important precursors of UDP-GlcNAc, glucosamine-6-phosphate (GlcN-6-P) and glucosamine-1-phosphate (GlcN-1-P). GlmM converts GlcN-6-P to GlcN-1-P, GlmU is a bifunctional enzyme, whereby GlmU converts GlcN-1-P to GlcNAc-1-P and then catalyzes the formation of UDP-GlcNAc from GlcNAc-1-P and uridine triphosphate. In the present study, methyl 2-amino-2-deoxyl-α-D-glucopyranoside 6-phosphate (1α), methyl 2-amino-2- deoxyl-β-D-glucopyranoside 6-phosphate (1β), two analogs of GlcN-6-P, were synthesized as GlmM inhibitors; 2-azido-2-deoxy-α-D- glucopyranosyl phosphate (2) and 2-amino-2,3-dideoxy-3-fluoro-α- Dglucopyranosyl phosphate (3), analogs of GlcN-1-P, were synthesized firstly as GlmU inhibitors. Compounds 1α, 1β, 2, and 3 as possible inhibitors of mycobacterial GlmM and GlmU are reported herein. Compound 3 showed promising inhibitory activities against GlmU, whereas 1α, 1β and 2 were inactive against GlmM and GlmU even at high concentrations.
Sweets for catalysis - Facile optimisation of carbohydrate-based bis(oxazoline) ligands
Minuth, Tobias,Irmak, Mustafa,Groschner, Annika,Lehnert, Tobias,Boysen, Mike M. K.
experimental part, p. 997 - 1008 (2009/07/19)
A new type of carbohydrate-based bis(oxazoline) ligands was prepared from inexpensive D-glucosamine and tested in asymmetric cyclopropanation reactions. For optimisation, modified ligands with 3-O substituents of varying size and electronic properties were prepared as well as a 3-OH unprotected and a perpivaloylated derivative. All new ligands were tested in asymmetric cyclopropanation, revealing a strong dependence of enantioselectivity on steric demand and electronic properties of the 3-O residue. Also, a significant influence of the pyranose conformation, which is determined by the presence or absence of the cyclic acetal group, was observed. Thus, it was easily possible to tune the new carbohydrate bis(oxazoline) ligands to a given reaction.
Facile Preparation of Glycosyl Donors for Oligosaccharide Synthesis: 2-Azido-2-deoxyhexopyranosyl Building Blocks
Buskas, Therese,Garegg, Per J.,Konradsson, Peter,Maloisel, Jean-Luc
, p. 2187 - 2194 (2007/10/02)
Facile routes to the 2-azido-2-deoxy-1-thioglycosides 6, 7, 15, and 18 and of the 2-azido-2-deoxy-4-pentenoglycoside 11, are described.These are useful intermediates for the synthesis of oligo-saccharides containing α-D-2-amino-2-deoxy (or 2-acetamido-2-d
