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 spot within the literature, this is often the single sequence to hide this significant subject in natural and biochemistry. Drawing upon the mixed services of the overseas "who's who" in amino acid study, those volumes signify a true benchmark for amino acid chemistry, supplying a finished dialogue of the prevalence, makes use of and functions of amino acids and, through extension, their polymeric types, peptides and proteins.

The functional worth of every quantity is heightened by means of the inclusion of experimental procedures.


The five volumes conceal the next topics:

Volume 1: Origins and Synthesis of Amino Acids

Volume 2: converted Amino Acids, Organocatalysis and Enzymes

Volume three: construction Blocks, Catalysis and Coupling Chemistry

Volume four: defense Reactions, Medicinal Chemistry, Combinatorial Synthesis

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


The fourth quantity during this sequence is established 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 comprises, 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. tools, akin to phage reveal, 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 info could be considered here.

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

Example text

It has also been used to prepare several N-Boc-protected unnatural amino acids [99]. Boc-ON provides good yields of Boc-amino acids [100] and is more soluble in organic solvents. However, the oxime byproduct is water insoluble and is removed by extraction with Et2O. 34 Urethane protections derived from secondary alcohols. 35 Preparation of Na-Boc-amino acids. cially available as well as stable for long duration. Acidification of the alkali salt of Bocamino acids (and work up of N-Boc-protected compounds) is best done using 10% citric acid solution.

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.

Indeed, the discovery of this new method introduced what is now referred to as a “fourth dimension” to the protection schemes due to its compatibility with benzyl-based (removed by hydrogenolysis), tert-butyl-based (removed by acids), and 9-fluorenylmethyl-based (removed by bases) protections. The Aloc group 63 is introduced using allyl chloroformate (Aloc-Cl) or diallyl dicarbonate (Aloc)2O [88, 89]. 33). Allyl transfer to the deblocked amine is avoided by the addition of scavengers, which preferentially accept the allyl group from the palladium complex.

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