20787-14-8Relevant academic research and scientific papers
Synthesis of nortropane alkaloid calystegine B2 from methyl α-D-xylopyranoside
Underlin, Emilie N.,Jensen, Henrik H.
, p. 122 - 126 (2019/01/04)
A new synthetic route for formation of a central cycloheptanone intermediate leading to the nortropane alkaloid calystegine B2 is described. The approach installs the desired ketone functionality directly in a ring-closing metathesis step. The
Analysis of UDP-D-apiose/UDP-D-xylose synthase-catalyzed conversion of UDP-D-apiose phosphonate to UDP-D-xylose phosphonate: Implications for a retroaldol-aldol mechanism
Choi, Sei-Hyun,Mansoorabadi, Steven O.,Liu, Yung-Nan,Chien, Tun-Cheng,Liu, Hung-Wen
supporting information, p. 13946 - 13949 (2012/10/29)
UDP-d-apiose/UDP-d-xylose synthase (AXS) catalyzes the conversion of UDP-d-glucuronic acid to UDP-d-apiose and UDP-d-xylose. An acetyl-protected phosphonate analogue of UDP-d-apiose was synthesized and used in an in situ HPLC assay to demonstrate for the first time the ability of AXS to interconvert the two reaction products. Density functional theory calculations provided insight into the energetics of this process and the apparent inability of AXS to catalyze the conversion of UDP-d-xylose to UDP-d-apiose. The data suggest that this observation is unlikely to be due to an unfavorable equilibrium but rather results from substrate inhibition by the most stable chair conformation of UDP-d-xylose. The detection of xylose cyclic phosphonate as the turnover product reveals significant new details about the AXS-catalyzed reaction and supports the proposed retroaldol-aldol mechanism of catalysis.
Novel D-xylose derivatives stimulate muscle glucose uptake by activating AMP-activated protein kinase α
Gruzman, Arie,Shamni, Ofer,Yakir, Moriya Ben,Sandovski, Daphna,Elgart, Anna,Alpert, Evgenia,Cohen, Guy,Hoffman, Amnon,Katzhendler, Yehoshua,Cerasi, Erol,Sasson, Shlomo
supporting information; scheme or table, p. 8096 - 8108 (2009/12/07)
Type 2 diabetes mellitus has reached epidemic proportions; therefore, the search for novel antihyperglycemic drugs is intense. We have discovered that D-xylose increases the rate of glucose transport in a non-insulin-dependent manner in rat and human myot
A Study of the Rapid Anomerization of Poly-O-benzyl-β-D-glucopyranosides with Titanium Tetrachloride
Koto, Shinkiti,Morishima, Naohiko,Kawahara, Reiko,Ishikawa, Katsuhiko,Zen, Shonosuke
, p. 1092 - 1096 (2007/10/02)
Titanium tetrachloride rapidly anomerizes methyl 2,3,4,6-tetra-O-benzyl-β-D-glucopyranoside in dichloromethane at 25 deg C.Evidence for the proposal that the benzyloxymethyl group on C-5 and the ring oxygen of the glucoside cooperate to prompt the reaction is described.The reagent anomerizes the interglycosidic linkage of several disaccharide derivatives.
