884655-09-8Relevant articles and documents
Rapid synthesis of partially O-methylated alditol acetate standards for GC-MS: Some relative activities of hydroxyl groups of methyl glycopyranosides on Purdie methylation
Sassaki, Guilherme L.,Gorin, Philip A. J.,Souza, Lauro M.,Czelusniak, Phelipe A.,Iacomini, Marcello
, p. 731 - 739 (2005)
Mixtures containing the majority of partially O-methylated alditol acetates (PMAAs), necessary for the GC-MS based identification of glycosidic linkages in oligo- and polymeric structures were prepared. Rha, Fuc, Rib, Ara, Xyl, Man, Gal, and Glc were converted to their Me glycosides, and the products were progressively O-methylated using the Purdie reagent at 25°C. Resulting PMGs were assayed by TLC and at times that were optimum for formation of mono-O-methyl derivatives and later for higher degrees of methylation; they were converted to PMAAs, in a process incorporating NaB2H4 reduction. The majority of these can be used as standards for simultaneous identification of pyranosides and some furanosyl units particularly in heteropolysaccharides. The relative reactivities of OH-groups were determined by GC-MS as: Me α- and β-Glcp, HO-2 > HO-4 > HO-3 > HO-6, Me α- and β-Galp, HO-3 > HO-2 > HO-4 > HO-6, Me α-Manp, HO-3 > HO-2 > HO-4 > HO-6, Me β-Manp, HO-3 > HO-4 ≥ HO-6 > HO-2, Me α-Rhap, OH-3 > OH-2 > OH-4; Me αβ-Fucp, OH-2 > OH-3 > OH-4, and Me αβ-Xylp, OH-2 > OH-4 > OH-3. The results differ from those obtained with Haworth, Hakomori, and Ciucanu methylation techniques, although some similarities occurred with the more rapid Kuhn method.
Efficient isomerization of methyl arabinofuranosides into corresponding arabinopyranosides in presence of pyridine
Prabhakar, Sunchu,Lemiègre, Lo?c,Benvegnu, Thierry,Hotha, Srinivas,Ferrières, Vincent,Legentil, Laurent
, p. 63 - 66 (2016/07/22)
Fisher glycosylation, the oldest but efficient reaction towards alkyl glycosides, suffers nonetheless from lack of selectivity, especially when dealing with pentoses. In this case, a mixture of the four isomers, namely the furanosides and the pyranosides, is formed. According to previous studies, the rate and selectivity of the reaction depend greatly on the reaction time and the temperature. In this report, another factor was evaluated, the introduction of a weak nucleophilic base. Interestingly, addition of pyridine few hours after the reaction has started allowed rapid isomerization of the methyl pentofuranosides into its pyranoside counterparts. The reaction proceeds with great diastereoselectivity using arabinose, ribose, xylose and lyxose as starting pentoses. Corresponding methyl pyranosides were obtained as the sole isomers with yields ranging from 65% to 75%.
Unexpected furanose/pyranose equilibration of N-glycosyl sulfonamides, sulfamides and sulfamates
Suthagar, Kajitha,Polson, Matthew I. J.,Fairbanks, Antony J.
, p. 6573 - 6579 (2015/06/16)
De-protected arabino N-glycosyl sulfamides, sulfonamides and sulfamates were found to mutarotate and convert from the furanose to the thermodynamically more stable pyranose form in aqueous solution. The presence of a strongly electron withdrawing group in
Synthesis of methyl 5-S-alkyl-5-thio-d-arabinofuranosides and evaluation of their antimycobacterial activity
Sanki, Aditya K.,Boucau, Julie,Srivastava, Parijat,Adams, Samuel S.,Ronning, Donald R.,Sucheck, Steven J.
, p. 5672 - 5682 (2008/12/21)
The emergence of drug resistant tuberculosis necessitates a search for new antimycobacterial compounds. The antigen 85 (ag85) complex is a family of mycolyl transferases involved in the synthesis of trehalose-6,6′-dimycolate and the mycolated hexasacchari
