PMID: 9440042Jan 24, 1998Paper

Esterification of 9-fluorenylmethoxycarbonyl-glycosylated serine and cysteine derivatives with an hydroxymethyl resin

The Journal of Peptide Research : Official Journal of the American Peptide Society
E Harth-Fritschy, D Cantacuzène

Abstract

Esterification of glycosylated serine and cysteine derivatives with a 4-alkoxybenzyl alcohol (Wang) resin is described. The classical methods of ester bond formation (symmetrical anhydride, 2-(1H-benzotriazol-1-yl)-1,1,3,3-tetramethyluronium tetrafluoroborate [TBTU]/4-dimethylaminopyridine [DMAP] with or without 1-hydroxybenzotriazole [HOBT], pentafluorophenyl [Pfp] esters gave high percentages of racemization of the glycosylated serine or cysteine residues. To reduce the D-amino acid content, we found that the best results were obtained with the highly efficient MSNT reagent (2,4,6-mesitylenesulfonyl-3-nitro-1,2,4-triazolide), which gave a high yield of substitution of the resin and the lowest percentage of racemization. A difference in behavior was observed between the two amino acids. The glycosylated cysteine derivative always gave lower racemization than the analogous glycosylated serine.

References

Feb 28, 1986·Cell·E Ruoslahti, M D Pierschbacher
Mar 1, 1989·Biological Chemistry Hoppe-Seyler·D AmbrosiusH Zahn
Jan 1, 1982·Cancer Metastasis Reviews·I R Hart
Jan 1, 1994·Advances in Carbohydrate Chemistry and Biochemistry·H G GargH Kunz
Jul 1, 1996·Journal of Peptide Science : an Official Publication of the European Peptide Society·F SiedlerL Moroder

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Citations

Aug 26, 1998·The Journal of Peptide Research : Official Journal of the American Peptide Society·E Harth-FritschyD Cantacuzène
Jul 17, 2018·Journal of Peptide Science : an Official Publication of the European Peptide Society·Risa TakayamaFayna Garcia-Martin
May 26, 2021·Chemistry : a European Journal·Veselin NasufovićHans-Dieter Arndt

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