The synthesis of glycopeptide fragments of human plasma alpha1-acid glycoproteins by sequential elongation at the terminal-amino group.

Carbohydrate Research
M A Shaban, R W Jeanloz

Abstract

Glycopeptides corresponding to sequences 27--28, 48--49, and 58--59 of human plasma alpha1-acid glycoproteins have been synthesized by sequential elongation of the peptide chain at the terminal amino group. 2-Acetamido-3,4,6-tri-O-acetyl-1-N-(L-aspart-4-oyl)-2-deoxy-beta-D-glucopyranosylamine was condensed with the p-nitrophenyl esters of protected amino acids to give the corresponding protected glycodipeptides having the sequences Gly-(GlcNAc-4-)Asn, Pro-(GlcNAc-4-)Asn, Val-(GlcNAc-4-)Asn, Leu-(GlcNAc-4-)Asn, Glu-(GlcNAc-4-)Asn, Tyr-(GlcNAc-4-)Asn, Ser-(GlcNAc-4-)Asn, and Cys-(GlcNAc-4-)Asn. Deprotection of the carbohydrate and of the peptide residues of these compounds was achieved, except for those having N-tert-butyloxycarbonyl protective groups, to give the corresponding free glycopeptides. The glycotripeptide 2-acetamido-1-N-(2-N-[N-(tert-butyloxycarbonyl)-L-glutam-1-oyl-L-tyrosyl]-L-aspart-4-oxy)-2-deoxy-beta-D-glucopyranosylamine, having the amino acid sequence 10--12 of human plasma alpha1-acid glycoprotein, was prepared by condensation of 2-acetamido 3,4,6-tri-O-acetyl-2-deoxy-1-N-[2-N-(L-tyrosyl)-L-aspart-4-oyl[-beta-D-glucopyranosylamine with 5-benzyl 1-p-nitrophenyl N-(tert-butyloxycarbonyl)-L-glutamate, followed b...Continue Reading

References

May 18, 1971·Biochimica Et Biophysica Acta·H SinoaraA Fukui
Jan 22, 1971·Biochemical and Biophysical Research Communications·K SchmidT Motoyama
Oct 1, 1971·Biochemical and Biophysical Research Communications·T SukenoF Maley
Jan 15, 1969·Journal of the American Chemical Society·B Gutte, R B Merrifield
Jan 15, 1969·Journal of the American Chemical Society·R HirschmannR G Denkewalter

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Citations

Dec 1, 1976·Carbohydrate Research·M A Shaban, R W Jeanloz
Jan 1, 1981·CRC Critical Reviews in Biochemistry·J D Aplin, J C Wriston
Dec 1, 1976·Carbohydrate Research·M A Shaban, R W Jeanloz

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