20847-05-6Relevant articles and documents
6-Azido-6-deoxy-l-idose as a Hetero-Bifunctional Spacer for the Synthesis of Azido-Containing Chemical Probes
Hamagami, Hiroki,Kumazoe, Motofumi,Yamaguchi, Yoshiki,Fuse, Shinichiro,Tachibana, Hirofumi,Tanaka, Hiroshi
supporting information, p. 12884 - 12890 (2016/08/30)
The design of 6-azido-6-deoxy-l-idose for use as a hetero-bifunctional spacer is reported. The hemiacetal at one terminus is an equivalent of an aldehyde and can react with nucleophiles, such as amino groups and electron-rich aromatics. The azido group at the other terminus bio-orthogonally undergoes a Hüisgen [3+2] cycloaddition with an acetylene. The idose derivative exhibited a higher level of reactivity towards oxime formation than a corresponding glucose derivative. The13C NMR spectrum of the uniformly13C-labeled 6-azido-idose indicated that the acyclic forms of the sugar totaled 0.3 % of all the isomers, whereas those of glucose totaled 0.01 %. The larger population of the acyclic forms of the idose derivative would result in higher reactivity towards electrophilic addition in comparison with glucose derivatives. Finally, we prepared a C-idosyl epigallocatechin gallate (EGCG) that bears an azido group through C-glycosylation of EGCG with 6-azido-idose. This glycosyl form of the C-idosyl EGCG exhibited a cytotoxicity against U266 cells that was comparable to that of EGCG. These results suggested that the EGCG derivative could be used as an effective chemical probe for the elucidation of EGCG biological functions.
Model for antibiotic optimization via neoglycosylation: Synthesis of liponeoglycopeptides active against VRE
Griffith, Byron R.,Krepel, Candace,Fu, Xun,Blanchard, Sophie,Ahmed, Aqeel,Edmiston, Charles E.,Thorson, Jon S.
, p. 8150 - 8155 (2008/02/11)
The neoglycosylation of a methoxyamine-appended vancomycin aglycon with all possible N′-decanoylglucopyranose and N′-biphenoylglucopyranose regioisomers led to the production of a focused set of liponeoglycopeptide variants in good yields and with excellent stereoselectivity. High-throughput antibacterial assays employing a unique set of vancomycin-resistant Enterococci faecalis and Enterococci faecium clinical isolates revealed that the nature and regiochemistry of glycosyl lipidation modulated vancomycin-resistent Enterococci potency. In contrast to prior work with lipoglycopeptides, this study reveals the glucose C3′ or C4′ as the optimal position for neoglycopeptide lipidation. This purely chemical method for the diversification of the glycolipid portion of lipoglycopeptide antibiotics is simple to perform on a large scale, requires minimal synthetic effort in sugar donor preparation, and provides access to highly active antibiotics that are not easily prepared by other state-of-the-art methods.
The direct synthesis of 6-amino-6-deoxyaldonic acids as monomers for the preparation of polyhydroxylated nylon 6
Chaveriat, Ludovic,Stasik, Imane,Demailly, Gilles,Beaupere, Daniel
, p. 1349 - 1354 (2007/10/03)
6-Azido-6-deoxy-d-galactitol and d-mannitol were obtained quantitatively via the reduction of the corresponding 6-azido-6-deoxy-d-hexono-1,4-lactones, and 6-azido-6-deoxy-d-glucitol was obtained by the reduction of 6-azido-6-deoxyglucose in good yields. The reduction of monoazidodeoxyhexitols by catalytic hydrogenation gave the monoaminohexitol analogues in 95-98% yields. Oxidation of these afforded the corresponding 6-amino-6-deoxy-d-aldonic acids in moderate yields. Alternatively, saponification of 6-azido-6-deoxy-d-hexonolactones gave 6-azido-6-deoxyaldonic acid salts which, after reduction followed by neutralization, led to the expected compounds in 82-88% overall yields.
