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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 Proteïnes Cisteïna Catàlisi Peptide synthesis Proteins Cysteine Catalysis |
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: https://doi.org/10.3390/molecules18055155 |
It is part of: | Molecules, 2013, vol. 18, num. 5, p. 5155-5162 |
URI: | http://hdl.handle.net/2445/152584 |
Related resource: | https://doi.org/10.3390/molecules18055155 |
ISSN: | 1420-3049 |
Appears in Collections: | Articles publicats en revistes (Química Inorgànica i Orgànica) |
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