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Title: Understanding acid lability on Cysteine protecting groups
Author: Ramos Tomillero, Iván
Mendive Tapia, Lorena
Góngora Benítez, Miriam
Nicolás Galindo, Ernesto
Tulla-Puche, Judit
Albericio Palomera, Fernando
Keywords: Síntesi de pèptids
Peptide synthesis
Issue Date: 6-May-2013
Publisher: MDPI
Abstract: Cys-disulfide bonds contribute to the stabilization of peptide and protein structures. The synthesis of these molecules requires a proper protection of Cys residues, which is crucial to prevent side-reactions and also to achieve the correct Cys connectivity. Here we undertook a mechanistic study of a set of well-known acid-labile Cys protecting groups, as well other new promising groups, in order to better understand the nature of their acid-lability. The stability of the carbocation generated during the acid treatment was found to have a direct impact on the removal of the protective groups from the corresponding protected Cys-containing peptides. Hence a combination of steric and conjugative effects determines the stability of the carbocations generated. Here we propose diphenylmethyl (Dpm) as a promising protecting group on the basis of its intermediate relative carbocation stability. All the optimized geometries and energies presented in this study were determined using a B3LYP/6-31G(d,p) calculation. The results discussed herein may be of broader applicability for the development of new protecting groups.
Note: Reproducció del document publicat a:
It is part of: Molecules, 2013, vol. 18, num. 5, p. 5155-5162
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ISSN: 1420-3049
Appears in Collections:Articles publicats en revistes (Química Inorgànica i Orgànica)

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