191849-79-3Relevant academic research and scientific papers
Glycosylated analogs of formaecin I and drosocin exhibit differential pattern of antibacterial activity
Talat, Sariya,Thiruvikraman, Menithalakshmi,Kumari, Saroj,Kaur, Kanwal J.
, p. 537 - 555 (2014/02/14)
The synthetic glycopeptides are interesting model systems to study the effect of O-glycosylation in modulating their function and structure. A series of glycosylated analogs of two antibacterial peptides, formaecin I and drosocin, were synthesized by varying the nature of sugar and its linkage with bioactive peptides to understand the influence of structure variation of glycosylation on their antibacterial activities. Higher antibacterial activities of all glycopeptides compared to their respective non-glycosylated counterparts emphasize in part the importance of sugar moieties in functional implications of these peptides. The consequences of the unique differences among the analogs were apparent on their antibacterial activities but not evident structurally by circular dichroism studies. We have shown that differently glycosylated peptides exhibit differential effect among each other when tested against several Gram-negative bacterial strains. The change of monosaccharide moiety and/or its anomeric configuration in formaecin I and drosocin resulted into decrease in the antibacterial activity in comparison to that of the native glycopeptide, but the extent of decrease in antibacterial activity of glycosylated drosocin analogs was less. Probably, the variation in peptide conformation arising due to topological dissimilarities among different sugars in the same peptide resulting in possible modulation in binding properties appears to be responsible for differences in their antibacterial activities. Indeed, these effects of glycosylation are found to be sequence-specific and depend in the milieu of amino acid residues. Interestingly, none of the carbohydrate variants affected the basic property of these peptides, which is non-hemolytic and non-toxicity to eukaryotic cells. The Author(s) 2011.
From solution phase to "on-column" chemistry: Trichloroacetimidate-based glycosylation promoted by perchloric acid-silica
Mukhopadhyay, Balaram,Maurer, Sarah V.,Rudolph, Nadine,Van Well, Renate M.,Russell, David A.,Field, Robert A.
, p. 9059 - 9062 (2007/10/03)
Activation of ester-protected glycosyl trichloroacetimidate donors by perchloric acid immobilized on silica afforded 1,2-trans disaccharides in 60-90% yields. Applying this approach to one-pot sequential glycosylation resulted in efficient syntheses of th
Solid-phase synthesis of O-linked glycopeptide analogues of enkephalin
Mitchell,Pratt,Hruby,Polt
, p. 2327 - 2342 (2007/10/03)
The synthesis of 18 N-α-FMOC-amino acid glycosides for solid-phase glycopeptide assembly is reported. The glycosides were synthesized either from the corresponding O'Donnell Schiff bases or from N-α-FMOC-amino protected serine or threonine and the appropriate glycosyl bromide using Hanessian's modification of the Koenigs-Knorr reaction. Reaction rates of D-glycosyl bromides (e.g., acetobromoglucose) with the L- and D-forms of serine and threonine are distinctly different and can be rationalized in terms of the steric interactions within the two types of diastereomeric transition states for the D/L and D/D reactant pairs. The N-α-FMOC-protected glycosides [monosaccharides Xyl, Glc, Gal, Man, GlcNAc, and GalNAc; disaccharides Gal-β(1-4)-Glc (lactose), Glc-β(1-4)-Glc (cellobiose), and Gal-α(1-6)-Glc (melibiose)] were incorporated into 22 enkephalin glycopeptide analogues. These peptide opiates bearing the pharmacophore H-Tyr-c[DCys-Gly-Phe-DCys]- were designed to probe the significance of the glycoside moiety and the carbohydrate-peptide linkage region in blood-brain barrier (BBB) transport, opiate receptor binding, and analgesia.
Glycosylation of Fmoc amino acids: Preparation of mono- and di-glycosylated derivatives and their incorporation into Arg-Gly-Asp (RGD)-containing glycopeptides
Vegad, Hiran,Gray, Charles J.,Somers, Peter J.,Dutta, Anand S.
, p. 1429 - 1441 (2007/10/03)
Compounds containing O-glycosidic linkages between carbohydrate species (D-glucopyranose, D-mannopyranose and L-rhamnopyranose) and hydroxy-containing amino acid components (L-threonine, L-serine and L-hydroxyproline) have been synthesized. Significant qu
