Cyclotetrapeptides are constrained cyclic peptides whose synthesis is considered a difficult task. A methodology based on head-to-tail on-resin cyclization by anchoring the side-chain of trifunctional amino acids was investigated. A series of model cyclotetrapeptides containing the RGD sequence cyclo(Xaa-Arg-Gly-Asp) (Xaa = Ala, Phe, Phg, D-Ala, D-Phe, D-Phg) was synthesized with no cyclodimerization by-products. An evaluation and optimization study of all the parameters directly involved in the ring closure of constrained cyclopeptides was performed.

On-resin head-to-tail cyclization of cyclotetrapeptides: optimization of crucial parameters / M.C. Alcaro; G. Sabatino; J. Uziel; M. Chelli; M. Ginanneschi; P. Rovero; A.M. Papini. - In: JOURNAL OF PEPTIDE SCIENCE. - ISSN 1075-2617. - STAMPA. - 10:(2004), pp. 218-228. [10.1002/psc.512]

On-resin head-to-tail cyclization of cyclotetrapeptides: optimization of crucial parameters

M. C. Alcaro;SABATINO, GIUSEPPINA;M. Ginanneschi;ROVERO, PAOLO;PAPINI, ANNA MARIA
2004

Abstract

Cyclotetrapeptides are constrained cyclic peptides whose synthesis is considered a difficult task. A methodology based on head-to-tail on-resin cyclization by anchoring the side-chain of trifunctional amino acids was investigated. A series of model cyclotetrapeptides containing the RGD sequence cyclo(Xaa-Arg-Gly-Asp) (Xaa = Ala, Phe, Phg, D-Ala, D-Phe, D-Phg) was synthesized with no cyclodimerization by-products. An evaluation and optimization study of all the parameters directly involved in the ring closure of constrained cyclopeptides was performed.
2004
10
218
228
M.C. Alcaro; G. Sabatino; J. Uziel; M. Chelli; M. Ginanneschi; P. Rovero; A.M. Papini
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Utilizza questo identificatore per citare o creare un link a questa risorsa: https://hdl.handle.net/2158/373343
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