Glyco-Amino Acids HEADING_TITLE

Glyco-amino acids are incorporated into glycopeptides and glycoproteins that play essential roles in cell-cell recognition, fertilization and the docking of viruses and bacteria onto cells. Glycopeptides and glycoproteins also are important in the immune system, the endocrine system and development of the brain. Glycopeptide analogs of analgesic peptides have significantly improved metabolic stability and enhanced drug delivery.

Inserting Ser(Glc) into an analgesic peptide significantly improved the metabolic stability of the peptide and enhanced its drug delivery. (Yamamoto, T.; et. al. J.Med Chem. 2009, 52, 5164-75. The glycosylated Leu-enkephalin H-Tyr-D-Thr-Gly-Phe-Leu-Ser(beta-D-Glc)-NH2 produces an analgesic effect similar to morphine but with reduced dependence (Bilsky, EJ.; et. al. J. Med. Chem. 2000, 43, 2586-90). MMP2200, a leu-enkepalin analog containing Ser(beta-D-Lact), is approximately 10-fold more potent than the parent compound and may be a promising lead in the development of glycosylated peptides as analgesic drugs (Do Camero P.G.; et al J. Pharmacol. Exp. Ther. 2008, 326, 939-48).

Glycopeptide analogs of tuftsin derivatives containing Thr(beta-D-Glc) have been reported (Filira F.; et. al. Int. J. Pept. Protein Res. 1990, 36, 86-76). H-Thr(Glc)-Lys-Pro-Arg-OH binds better than tuftsin but lacks the ability to stimulate phagocytosis (Rocchi R.: et. al. J. Pept. Protein Res. 1987, 29, 262-75).

Glyco-amino acids used in solid phase peptide synthesis are Fmoc protected with the sugar generally protected as the fully acetylated form.

Glyco-amino acid derivatives from AAPPTec are of the highest quality and very affordably priced. These glyco-amino acid building blocks are suitably protected for peptide synthesis using Fmoc-protection.

AAPPTec can provide these products in bulk quantities.  Please send an e-mail to sales@aapptec.com for a quotation or use the On-Line Quotation Request.


 

Fmoc-Phenylalaninol