20298-35-5Relevant articles and documents
SYNTHESES OF 2-O-GLYCOSYL DERIVATIVES OF N-ACETYL-D-NEURAMINIC ACID
Ogura, Haruo,Furuhata, Kimio,Itoh, Masayoshi,Shitori, Yoshiyasu
, p. 37 - 52 (1986)
Syntheses of N-acetyl-D-neuraminic acid derivatives are reported.Methyl 4,7,8,9-tetra-O-acetyl-N-acetyl-2-chloro-2-deoxy-β-D-neuraminate (3) was prepared directly from methyl N-acetyl-β-D-neuraminate (2) in good yield.Koenigs-Knorr reaction of 3 with an excess of methanol gave the methyl α-glycoside of methyl N-acetyl-D-neuraminate (4). 2,3-O-Isopropylidene-D-ribono-1,4-lactone, 2,3-O-isopropylideneuridine, and 5-fluor-2,3-O-isopropylideneuridine reacted with 3 to give anomeric mixtures of methyl N-acetyl-D-neuraminate derivatives.The stereochemistry of these compounds was confirmed from n.m.r. and c.d. spectra, and measurements of the rate of hydrolysis of the glycosidic bond.
One pot synthesis of thio -glycosides via aziridine opening reactions
Hribernik, Nives,Tamburrini, Alice,Falletta, Ermelinda,Bernardi, Anna
supporting information, p. 233 - 247 (2021/01/14)
A one-pot aziridine opening reaction by glycosyl thiols generated in situ from the corresponding anomeric thio-acetates affords thio-glycosides with a pseudo-disaccharide structure and an N-linked tether. The scope of the one-pot aziridine opening reaction was explored on a series of mono- and disaccharides, creating a class of pseudo-glycosidic compounds with potential for further functionalization. Unexpected anomerization of glycosyl thiols was observed under the reaction conditions and the influence of temperature, base and solvent on the isomerization was investigated. Single isomers were obtained in good to acceptable yields for mannose, rhamnose and sialic acid derivatives. The class of thio-glycomimetics synthesized can potentially be recognized by various lectins, while presenting hydrolytic and enzymatic stability. The nitrogen functionality incorporated in the glycomimetics can be exploited for further functionalization, including tethering to linkers, scaffolds or peptide residues.
Addition of Sialic Acid to Insulin Confers Superior Physical Properties and Bioequivalence
Kabotso, Daniel E. K.,Kabotso, Daniel E. K.,Smiley, David,Mayer, John P.,Gelfanov, Vasily M.,Perez-Tilve, Diego,Dimarchi, Richard D.,Pohl, Nicola L. B.,Liu, Fa
, p. 6134 - 6143 (2020/07/10)
Native insulin is susceptible to biophysical aggregation and fibril formation, promoted by manual agitation and elevated temperatures. The safety of the drug and its application to alternative forms of administration could be enhanced through the identification of chemical modifications that strengthen its physical stability without compromising its biological properties. Complex polysialic acids (PSAs) exist naturally and provide a means to enhance the physical properties of peptide therapeutics. A set of insulin analogues site-specifically derivatized with sialic acid were prepared in an overall yield of 50-60%. Addition of a single or multiple sialic acids conferred remarkable enhancement to the biophysical stability of human insulin while maintaining its potency. The time to the onset of fibrillation was extended by more than 10-fold relative to that of the native hormone. These results demonstrate that simplified sialic acid conjugates represent a viable alternative to complex natural PSAs in increasing the stability of therapeutic peptides.
