Search results for "glycopeptide"

HYCRON, an Allylic Anchor for High-Efficiency Solid Phase Synthesis of Protected Peptides and Glycopeptides

1997

The recently developed allylic HYCRON anchor1 exhibits excellent properties for the solid phase synthesis of protected peptides and glycopeptides. Model reactions with analogous low molecular weight compounds assessed the acid- and base-stability of the polar and flexible HYCRON linkage. The new anchor is available in a two-step synthesis and allows the use of both the Boc- and the Fmoc-strategy, which can even be combined within one synthesis. Protected glycopeptides are released under almost neutral conditions, taking advantage of the Pd(0)-catalyzed allyl transfer to a weakly basic nucleophile such as N-methylaniline. The highly efficient synthesis of O-αGalNAc(TN)-peptides of the MUC-1 …

Synthetic Glycopeptides for the Development of Antitumour Vaccines

2003

Glycoproteins of tumour cells often are aberrantly glycosylated. In its tumour-associated form, the epithelial mucin MUC1 carries short saccharide structures such as TN, T, sialyl-TN, and sialyl-T antigens. Due to the incomplete saccharide components, peptide epitopes of the backbone become accessible to the immune system. For the construction of synthetic antitumour vaccines, glycopeptides have been synthesized which contain tumour-associated saccharide antigens and peptide sequences from the tandem repeat portion of MUC1. In the synthesis of these glycopeptides, preformed glycosyl–amino acid building blocks are applied in solution- or solid-phase strategies. Examples are given for the use…

Enzymatische hydrolyse hydrophiler ester durch lipasen - eine milde carboxydeblockierung von peptiden und glycopeptiden

1993

Abstract The markedly hydrophilic 2-(N-morpholino)ethyl (MoEt) esters of protected peptides and glycopeptides are selectively and efficiently cleaved by lipases in water/acetone (10:1) at pH 7.

Synthesis of Glycopeptides Containing Carbohydrate and Peptide Recognition Motifs

2000

Fluorenylmethoxycarbonyl-ProtectedO-Glycosyl-N-methyl Amino Acids: Building Blocks for the Synthesis of Conformationally Tuned Glycopeptide Antigens

2015

Peptide antibiotics often contain N-methylated amino acids. These N-methylamino components enhance the metabolic stability and strongly influence the conformational behavior of these peptide drugs. N-Methyl-O-glycosyl amino acids, in particular, threonine and serine derivatives, are unknown so far. Fmoc-protected N-methyl-O-glycosyl-threonine and -serine building blocks, including sialyl TN antigens, have been synthesized for the first time by converting the Fmoc-protected O-glycosyl amino acids or their tert-butyl esters into the corresponding oxazolidinones followed by reductive ring-opening. These new components are considered interesting for the construction of modified mucin glycopepti…

Chemical and enzymatic synthesis of glycopeptides

1995

Progress recently made in the synthesis of biologically relevant N- and O-glycopeptides is illustrated by examples. In this context, developments in the preparation of complex saccharide side chains and in the subsequent coupling to peptide portions is described. Special emphasis is given to the synthesis of Lewis antigen-type structures. Furthermore, modern methods in solid phase peptide syntheses utilizing glycosylated building blocks are presented. Recent advances in glycopeptide syntheses employing enzymatic methods in deprotection steps as well as in peptide/saccharide chain elongation are reported.

Der (2-Phenyl-2-trimethylsilyl)ethyl(PTMSEL)-Linker - ein neuer, mit Fluorid spaltbarer Anker für die Festphasensynthese von geschützten Peptiden und…

2002

ChemInform Abstract: Synthesis of Glycopeptide Partial Structures of Virus Coat Glycoproteins

2010

Structure analysis of acetylated and non-acetylated O-linked MUC1-glycopeptides by post-source decay matrix-assisted laser desorption/ionization mass…

1997

We have investigated the potential of structural elucidation of O-linked glycopeptides by post-source decay matrix-assisted laser desorption ionization mass spectrometry (PSD-MALDI-MS). In order to establish detailed fragmentation patterns and to dissect fragment ions with and without carbohydrate content, the same O-linked MUC1-derived glycopeptides with acetylated and non-acetylated sugars were analysed and compared. Furthermore, we were interested to examine possible differences in the fragmentation between glycopeptides with acetylated and non-acetylated sugars. The obtained PSD-MALDI-MS spectra showed a rather complete set of fragmentation data which allows us to localize the glycan on…

Sulfated and Non-Sulfated Glycopeptide Recognition Domains of P-Selectin Glycoprotein Ligand 1 and their Binding to P- and E-Selectin

2009

Total synthesis through block glycosylation and selective chemical O-sulfation of tyrosine residues yielded the glycopeptide recognition domain A (X=SO(3) (-)) of the P-selectin glycoprotein ligand 1, in which the terminal sialic acid of the complex hexasaccharide side chain was replaced by (S)-cyclohexyl lactic acid. In binding assays the O-sulfated structure A showed high affinity towards P-selectin, the non-sulfated towards E-selectin.