Amino Acids, Peptides and Proteins in Organic Chemistry 3: by Andrew B. Hughes

By Andrew B. Hughes

This is the 3rd of 5 books within the Amino Acids, Peptides and Proteins in natural Synthesis series. 

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

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


The five volumes disguise the next 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: defense Reactions, Medicinal Chemistry, Combinatorial Synthesis

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


This 3rd quantity within the sequence provides a detailed account of modern advancements within the (bio-)synthesis of amino acids and peptides. Divided into elements, the 1st part offers with amino acids as construction blocks, together with the iteration of alpha-amino acids, beta-lactams, and heterocycles. the second one part is dedicated to the synthesis of peptides, with the focal point on stable section synthesis. although, resolution part peptide synthesis is roofed to boot, as are themes reminiscent of coupling reagents, chemical ligation, peptide purification and automation.


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

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

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Additional info for Amino Acids, Peptides and Proteins in Organic Chemistry 3: Building Blocks, Catalysis and Coupling Chemistry (Amino Acids, Peptides and Proteins in Organic Chemistry (VCH))

Example text

This transformation occurs in a two-step process that exemplifies the third general mechanism of amine transfer in metabolism (after GAT and PLP action) – ligation of the a-amino group of aspartate and then elimination of fumarate, which is recycled via the TCA cycle [147]. Argininosuccinate synthetase is homologous to asparagine synthetase [148] and uses ATP to activate the urea by adenylation [149]; nucleophilic substitution by aspartate produces argininosuccinate. Argininosuccinate lyase, the terminal enzyme of the pathway, is a member of a family of aspartase enzymes that catalyze the elimination of fumarate (which feeds into the TCA cycle) from aspartate and N-aspartyl derivatives [150, 151], demonstrating the generality of this two step synthetase/lyase route for the indirect transfer of ammonia – the third general process for transfer of nitrogen between metabolites.

Most plants and microbes transfer the sulfur from cysteine to an activated homoserine derivative to make homocysteine, which is then methylated to produce methionine. In mammals only the reverse process is carried out. Some fungi undertake transsulfuration in both directions [116, 117]. The interconversion of cysteine and homocysteine involves facilitating leaving group chemistry at b- and c-positions in two sequential PLP-dependent processes: cystathionine c-synthase and cystathionine b-lyase (forward) or cystathionine b-synthase then cystathionine c-lyase (reverse).

This enzyme is a homodimer with an active-site PLP cofactor bound to Lys41. The initial stages of the reaction parallel those of aminotransferase enzymes. The monoanion form of OAS forms a Schiff base with PLP by amino exchange with Lys41, which is thereby liberated to act as an active-site acid–base catalyst. In this case, deprotonation of the a-center of PLP-linked OAS by Lys41 eliminates acetate and forms of a bound aminoacrylyl intermediate. After loss of acetate, hydrosulfide binds, in the second step of this ordered Ping Pong Bi Bi mechanism, and reacts with the aminoacrylate intermediate to produce cysteine.

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