Combinatorial Solid-Phase Synthesis of Multivalent Cyclic Neoglycopeptides.

@article{Wittmann2000CombinatorialSS,
  title={Combinatorial Solid-Phase Synthesis of Multivalent Cyclic Neoglycopeptides.},
  author={Valentin Wittmann and Sonja Seeberger},
  journal={Angewandte Chemie},
  year={2000},
  volume={39 23},
  pages={
          4348-4352
        }
}
8: Boc-Lys(Aloc)-Orn(Ddv)-Gly-Ala-D-Lys(Ddv)-Orn(Ddv)-D-Val-Glu(OAll)-Bal-Sieber-TG (0.54 g, 70 μmol) was shaken for 16 h under argon with morpholine (77 μl, 0.88 mmol) and Pd(PPh3)4 (12 mg, 10 μmol) in DMF/DMSO (1:1) (3 mL) and subsequently washed with DMF and CH2Cl2. After treatment of a resin sample with the cleavage cocktail, remaining 8 was extracted with MeOH from the solid support. HPLC (20–80 % acetonitrile in water/0.1 % TFA over 30 min): retention time tR = 18.5 min; ESI-MS (M + H… Expand
Copper(II)-Mediated Activation of Sugar Oxazolines: Mild and Efficient Synthesis of β-Glycosides ofN-Acetylglucosamine
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References

SHOWING 1-10 OF 54 REFERENCES
Side-product formation during cyclization with HBTU on a solid support.
The coupling reagent 2-(1H-benzotriazol-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate (HBTU) was used in an attempt to prepare a highly strained 10-membered lactam ring on a solid support viaExpand
Constrained glycopeptide ligands for MPRs. Limitations of unprotected phosphorylated building blocks.
TLDR
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
Glycosylation with N-Troc-protected glycosyl donors.
TLDR
The N-Troc-protected donors gave pure beta-glycosides in somewhat higher yields than the N-Phth-protected counterparts, which allows selective N-deprotection in oligosaccharides containing both N- Troc and N- Phth groups. Expand
Synthetic O-glycopeptides as model substrates for glycosyltransferases
Abstract A new approach to O-glycopeptides of the glucosamine type is described. N-Urethane protected, peracetylated glucosamine is converted into its 1-thio (1-bromo) derivative and used forExpand
Cyclic peptide template combinatorial libraries: synthesis and identification of chymotrypsin inhibitors.
TLDR
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
Standard Fmoc protocols.
TLDR
This chapter describes standard protocols for Fmoc solid-phase peptide synthesis, which is the method of choice for the solid- phase synthesis of most modified peptide species including phosphorylated, sulfated, and glycosylated peptides. Expand
Syntheses and some applications of chemically defined multivalent glycoconjugates.
  • R. Roy
  • Chemistry, Medicine
  • Current opinion in structural biology
  • 1996
Classical multivalent neoglycoproteins have been widely used to study a great number of carbohydrate-protein interactions. The synthesis of other neoglycoconjugates with various shapes, valencies,Expand
Shiga-like toxins are neutralized by tailored multivalent carbohydrate ligands
TLDR
The crystal structure of the B5 subunit of Escherichia coli O157:H7 Shiga-like toxin I in complex with an analogue of its carbohydrate receptor is used to design an oligovalent, water-soluble carbohydrate ligand (named STARFISH), with subnanomolar inhibitory activity. Expand
Glycobiology in Medicine.
  • Y. Lee, R. Lee
  • Biology, Medicine
  • Journal of biomedical science
  • 1996
TLDR
Conjugation of polysaccharides derived from pathogenic micro-organisms with appropriate proteins provides effective vaccines against the micro- organisms and many pathogens use carbohydrates as recognition markers for invasion. Expand
Der Allyloxycarbonyl(aloc)‐Rest – die Verwandlung einer untauglichen in eine wertvolle Aminoschutzgruppe für die Peptidsynthese
Ce groupe protecteur permet la synthese efficace et selective de peptides sensibles (contenant la serine par exemple); il est elimine des esters peptidiques tels que Aloc-Phe-Ser (tBu)-OtBu, par uneExpand
...
1
2
3
4
5
...