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Amino Acids, Peptides and Proteins in Organic Chemistry, by Andrew B. Hughes

By Andrew B. Hughes

This is the fourth of 5 books within the Amino Acids, Peptides and Proteins in natural Synthesis series. 

Closing a niche within the literature, this can be the one sequence to hide this crucial subject in natural and biochemistry. Drawing upon the mixed services of the overseas "who's who" in amino acid examine, those volumes signify a true benchmark for amino acid chemistry, supplying a complete dialogue of the incidence, makes use of and purposes of amino acids and, by means of extension, their polymeric kinds, peptides and proteins.

The sensible worth of every quantity is heightened via the inclusion of experimental procedures.


The five volumes disguise the subsequent topics:

Volume 1: Origins and Synthesis of Amino Acids

Volume 2: converted Amino Acids, Organocatalysis and Enzymes

Volume three: development Blocks, Catalysis and Coupling Chemistry

Volume four: safeguard Reactions, Medicinal Chemistry, Combinatorial Synthesis

Volume five: research and serve as of Amino Acids and Peptides


The fourth quantity during this sequence is based in 3 major sections. the 1st part is ready safety reactions and amino acid dependent peptidomimetics. the second one, and such a lot vast, half is dedicated to the medicinal chemistry of amino acids. It contains, between others, the chemistry of alpha- and beta amino acids, peptide medicinal drugs, and advances in N- and O-glycopeptide synthesis. the ultimate half bargains with amino acids in combinatorial synthesis. equipment, equivalent to phage show, library peptide synthesis, and computational layout are described.


Originally deliberate as a six quantity sequence, Amino Acids, Peptides and Proteins in natural Chemistry now completes with 5 volumes yet continues to be complete in either scope and coverage.

Further information regarding the five quantity Set and buying information may be considered here.

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Additional info for Amino Acids, Peptides and Proteins in Organic Chemistry, Protection Reactions, Medicinal Chemistry, Combinatorial Synthesis (Volume 4)

Sample text

It also precludes the use of acid-labile solid supports. ii) The Fmoc group can be cleaved using mild reagents such as piperidine. iii) With Fmoc as protective function, the progress of reactions can be monitored through UV (lmax: 267, 290, 301 nm) and fluorescence spectrometry – a property that can be used to advantage in fully automated peptide synthesis. . Preparation: 9-Fluorenylmethyl chloroformate (Fmoc-Cl) 51 and Fmoc-OSu 52 are the favored reagents for introducing the Fmoc group. Fmoc-Cl is commercially available (also prepared by the action of phosgene on 9-fluorenylmethanol) and storable for a long time under anhydrous conditions at low temperature.

It spark-started the era of modern peptide synthesis. Until then the practice of peptide synthesis largely relied on the use of acyl groups for a-amino protection, whose selective removal without hydrolyzing the painstakingly assembled peptides was not always possible. In order to circumvent the problem of instability of peptide bonds in harsh deblocking conditions of Na-acyl groups, an approach of peptide chain extension from the amino-terminus (N ! C direction) was inevitably followed. Although, repetitive deblocking of Na protection could be avoided, the strategy offered several synthetic difficulties per se.

37) [121]. 3 Protection of the Nitrogen of a-Amino Acid N-Carboxy Anhydrides (NCAs) 122 N-Carboxy anhydrides (NCAs) 75 (Leuchs anhydrides or internal anhydrides of amino acids) represent simultaneously protected and activated amino acid derivatives. However, polymerization and rapid hydrolysis properties of NCAs make acylations involving them difficult. Nonetheless, protection of the nitrogen of NCAs converts them into efficient peptide coupling agents. Urethane-protected NCAs 76–78 (urethane-protected N-carboxy anhydrideUNCAs) are particularly advantageous since they retain the reactivity of NCAs, but exclude the possibility of oligomerization.

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