Amino Acid-Protecting Groups

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Amino acid-protecting groups.

Albert Isidro-Llobet, Mercedes Álvarez, Fernando Albericio Institute for Research in Biomedicine, Barcelona Science Park, Baldiri Reixac 10, 08028Barcelona, Spain. CIBER-BBN, Networking Centre on Bioengineering, Biomaterials and Nanomedicine, Barcelona Science Park, Baldiri Reixac 10, 08028-Barcelona, Spain. Laboratory of Organic Chemistry, Faculty of Pharmacy, University of Barcelona, 08028Bar...

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Protecting Groups, Acid, Base, Temperature and Time

Factors affecting aspartimide formation, such as protecting groups, acidity, basicity, and temperature, were studied using the model tetrapeptide, Glu-AspGly-Thr. The aspartyl carboxyl side chain in this tetrapeptide was either free or protected as a benzyl or cyclohexyl ester. Our results showed that the cyclohexyl ester led to far less aspartimide formation during acidic or tertiary amine tre...

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Understanding acid lability of cysteine protecting groups.

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 ord...

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Tunable acid-sensitive ester protecting groups in oligosaccharide synthesis.

A series of acid-cleavable ester-type protecting groups, with acid-sensitivity profiles parallel to those of 2-naphthylmethyl (NAP) or p-methoxybenzyl (PMB) ether, were designed and TFA in toluene was identified as a technically simple and effective deblocking cocktail for their global removal in the context of oligosaccharide synthesis.

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Novel Amino Protecting Group Chemistry

Functional group incompatibility in the synthesis of complex organic molecules has been a problem since the infancy of organic chemistry. Emil Fischer made a valuable contribution to organic chemistry when he came up with the notion that an otherwise reactive functional group could be temporarily rendered inert by attaching a suitable protecting group that could then later be removed [1]. Today...

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ژورنال

عنوان ژورنال: Chemical Reviews

سال: 2009

ISSN: 0009-2665,1520-6890

DOI: 10.1021/cr800323s