213400-35-2Relevant academic research and scientific papers
New Class of Glycoside Hydrolase Mechanism-Based Covalent Inhibitors: Glycosylation Transition State Conformations
Shamsi Kazem Abadi, Saeideh,Tran, Michael,Yadav, Anuj K.,Adabala, Pal John Pal,Chakladar, Saswati,Bennet, Andrew J.
supporting information, p. 10625 - 10628 (2017/08/15)
The design of covalent inhibitors in glycoscience research is important for the development of chemical biology probes. Here we report the synthesis of a new carbocyclic mechanism-based covalent inhibitor of an α-glucosidase. The enzyme efficiently catalyzes its alkylation via either an allylic cation or a cationic transition state. We show this allylic covalent inhibitor has different catalytic proficiencies for pseudoglycosylation and deglycosylation. Such inhibitors have the potential to be useful chemical biology tools.
Total synthesis of (+)-valienamine and (-)-1-epi-valienamine via a highly diastereoselective allylic amination of cyclic polybenzyl ether using chlorosulfonyl isocyanate
Li, Qing Ri,Kim, Seung In,Park, Sook Jin,Yang, Hye Ran,Baek, A Reum,Kim, In Su,Jung, Young Hoon
, p. 10384 - 10390 (2013/11/19)
The total synthesis of (+)-valienamine and (-)-1-epi-valienamine was concisely accomplished from readily available d-glucose via a highly diastereoselective amination of chiral benzylic ether using chlorosulfonyl isocyanate, intramolecular olefin metathesis, and diastereoselective reduction of cyclic enone using l-Selectride as the key steps.
FAMILY OF ARYL, HETEROARYL, O-ARYL AND O-HETEROARYL CARBASUGARS
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, (2012/12/13)
The present invention relates to a compound of the following formula (I): as well as its process of preparation, pharmaceutical and cosmetics composition comprising it and use thereof, notably as an inhibitor of the sodium-dependent glucose co-transporter, such as SGLTl, SGLT2 and SGLT3, in particular in the treatment or prevention of diabetes, and more particularly type-II diabetes, diabetes-related complications, such as arthritis of the lower extremities, cardiac infarction, renal insufficiency, neuropathy or blindness, hyperglycemia, hyperinsulinemia, obesity, hypertriglyceridemia, X syndrome and arteriosclerosis, as well as for its use as an anticancer, anti-infective, anti-viral, anti-thrombotic or anti- inflammatory drug, or for lightening, bleaching, depigmenting the skin, removing blemishes from the skin, particularly age spots and freckles, or preventing pigmentation of the skin.
Nucleotidylation of unsaturated carbasugar in validamycin biosynthesis
Yang, Jongtae,Xu, Hui,Zhang, Yirong,Bai, Linquan,Deng, Zixin,Mahmud, Taifo
scheme or table, p. 438 - 449 (2011/03/17)
Validamycin A is a member of microbial-derived C7N-aminocyclitol family of natural products that is widely used as crop protectant and the precursor of the antidiabetic drug voglibose. Its biosynthetic gene clusters have been identified in seve
Studies on the synthesis of valienamine and 1-epi-valienamine starting from d-glucose or l-sorbose
Cumpstey, Ian,Gehrke, Sebastian,Erfan, Sayeh,Cribiu, Riccardo
, p. 1675 - 1692 (2008/12/21)
Two synthetic routes to a carbocyclic precursor to valienamine are reported, starting from either d-glucose or l-sorbose and using ring-closing metathesis as a key step. A low-yielding synthesis of 1-epi-valienamine is reported. Results from an abortive third possible route to valienamine based on an early introduction of nitrogen are discussed.
Synthesis and biological evaluation of a bicyclo[4.1.0]heptyl analogue of glucose-1-phosphate
Dookhun, Veedeeta,Bennet, Andrew J.
, p. 1361 - 1364 (2007/10/03)
The synthesis of a bicyclo[4.1.0]heptyl analogue of glucose-1-phophate, (1R,2R,3S,4S,5S,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)-bicyclo[4.1.0] heptan-2-yl dihydrogen phosphate (5) is reported. The synthetic route chosen started with methyl α-D-glucopyranos
