Temporary attachment of carbohydrates to cyclopeptide templates : a new strategy for single-bead analysis of multivalent neoglycopeptides

  title={Temporary attachment of carbohydrates to cyclopeptide templates : a new strategy for single-bead analysis of multivalent neoglycopeptides},
  author={Valentin Wittmann and Sonja Seeberger and Hermann Schägger},
  journal={Tetrahedron Letters},
Abstract Employing a cleavable carbohydrate–peptide linker, a new strategy for single-bead analysis of multivalent cyclic neoglycopeptides based on Edman degradation is described. Edman degradation of glycopeptides is hampered by the acid lability of the glycosidic bond and potential incompatibilities of phenylthiohydantoin (PTH) derivatives of glycosylated amino acids with PTH derivatives of the proteinogenic amino acids. To overcome this problem, carbohydrates are detached from the… Expand
3 Citations

Figures from this paper

Synthesis and Application of Glycopeptide and Glycoprotein Mimetics
Glycosylation of proteins is the most complex form of posttranslational modification. Glycan chains of glycoproteins are involved in numerous biological recognition events, such as protein folding,Expand
Glycopeptide dendrimers. Part I
Glycopeptide dendrimers can be used as inhibitors of cell surface protein‐carbohydrate interactions, intervention with bacterial adhesion, for studying of recognition processes, diagnostics, imaging and contrast agents, mimetics, for complexation of different cationts, as site‐specific molecular delivery systems, for therapeutic purposes, as immunodiagnostics and in drug design. Expand


Constrained glycopeptide ligands for MPRs. Limitations of unprotected phosphorylated building blocks.
Although mannose disaccharides are required for optimal interaction, the detailed structure of the peptide template has a strong influence on binding to the receptor, and the restricted conformations of the cyclic peptides decreased the binding considerably. Expand
Cyclic peptide template combinatorial libraries: synthesis and identification of chymotrypsin inhibitors.
A cyclic peptide template combinatorial library in a positional scanning format, composed of three positional libraries, was synthesized using solid-phase chemistry and four orthogonal protecting groups to identify compounds with chymotrypsin inhibitory activity. Expand
Oligosaccharide Mimetics Obtained by Novel, Rapid Screening of Carboxylic Acid Encoded Glycopeptide Libraries
Glycopeptides that mimic the action of oligosaccharides have been rapidly identified through the implementation of combinatorial library methodology combined with a novel, easy, screening andExpand
Chemical glycobiology : Carbohydrates and glycobiology
Chemical tools have proven indispensable for studies in glycobiology and chemical approaches are contributing great insight into the myriad biological functions of oligosaccharides. Expand
Peptor’s backbone cyclization technology enables the creation of large ensembles of conformationally constrained peptidomimetic analogs by bridging any two positions along their backbones through bridges of varying sizes and chemical compositions. Expand
Glycopeptides as oligosaccharide mimics: high affinity sialopeptide ligands for sialoadhesin from combinatorial libraries.
The sialopeptide libraries were screened against the recombinant binding domain (SnD1) of a sialic acid binding Ig-like protein, sialoadhesin (Siglec-1), underscoring the importance of the carboxylic acid moiety for binding. Expand
The “One-Bead-One-Compound” Combinatorial Library Method
1. Peptoids 419 2. Oligocarbamates 420 3. Oligoureas 420 4. Vinylogous Sulfonyl Peptides 420 5. Peptidosulfonamides 420 6. Azatides 420 7. Ketides 420 D. Small Molecule Libraries 420 1. AcyclicExpand
General method for rapid synthesis of multicomponent peptide mixtures.
A method is suggested for the synthesis of multicomponent peptide mixtures with main point of modification that before every coupling cycle the resin is divided into equal parts and each portion is coupled with a different amino acid. Expand
A new type of synthetic peptide library for identifying ligand-binding activity
OUR aim was to improve techniques for drug development by facilitating the identification of small molecules that bind with high affinity to acceptor molecules (for example, cell-surface receptors,Expand
Clusters, bundles, arrays and lattices: novel mechanisms for lectin-saccharide-mediated cellular interactions.
The formation of lectin-saccharide lattices on the cell surface can organize the plasma membrane into specialized domains that perform unique functions. Expand