58769-74-7Relevant academic research and scientific papers
Aqueous Glycosylation of Unprotected Sucrose Employing Glycosyl Fluorides in the Presence of Calcium Ion and Trimethylamine
Pelletier, Guillaume,Zwicker, Aaron,Allen, C. Liana,Schepartz, Alanna,Miller, Scott J.
supporting information, p. 3175 - 3182 (2016/03/19)
We report a synthetic glycosylation reaction between sucrosyl acceptors and glycosyl fluoride donors to yield the derived trisaccharides. This reaction proceeds at room temperature in an aqueous solvent mixture. Calcium salts and a tertiary amine base promote the reaction with high site-selectivity for either the 3′-position or 1′-position of the fructofuranoside unit. Because nonenzymatic aqueous oligosaccharide syntheses are underdeveloped, mechanistic studies were carried out in order to identify the origin of the selectivity, which we hypothesized was related to the structure of the hydroxyl group array in sucrose. The solution conformation of various monodeoxysucrose analogs revealed the co-operative nature of the hydroxyl groups in mediating both this aqueous glycosyl bond-forming reaction and the site-selectivity at the same time.
Synthesis of 2',3',4'-trisphosphate-containing analogs of adenophostin A
Van Straten, Nicole C. R.,Van der Marel, Gijsbert A.,Van Boom, Jacques H.
, p. 6523 - 6538 (2007/10/03)
Adenophostin A analog 4 was prepared via trimethylsilyl trifluoromethanesulfonate (TMSOTf)-assisted glycosylation of (S)-6-N-diphenylacetyl-9-(2-tert-butyldiphenylsilyloxy-1- hydroxyprop-3-yl)-adenine (11) with trichloroacetimidate donor 12 to give dimer
Chemical Synthesis of Disaccharides which are Partial Structures of the Glycosaminoglycan Heparan Sulfate
Davis, Nicola J.,Flitsch, Sabine L.
, p. 359 - 368 (2007/10/02)
A specific tetradecasaccharide sequence (oligo-H, 1) of the proteoglycan heparan sulfate has recently been identified as being responsible for binding and activation of the basic fibroplast growth factor (bFGF), a potent mitogen.We present here the first
