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 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 examine, those volumes symbolize a true benchmark for amino acid chemistry, offering a entire dialogue of the incidence, makes use of and purposes of amino acids and, via extension, their polymeric varieties, peptides and proteins.

The useful price of every quantity is heightened through the inclusion of experimental procedures.


The five volumes hide the subsequent topics:

Volume 1: Origins and Synthesis of Amino Acids

Volume 2: changed Amino Acids, Organocatalysis and Enzymes

Volume three: development Blocks, Catalysis and Coupling Chemistry

Volume four: safety Reactions, Medicinal Chemistry, Combinatorial Synthesis

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


The fourth quantity during this sequence is dependent in 3 major sections. the 1st part is set safety reactions and amino acid dependent peptidomimetics. the second one, and so much large, 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 offers with amino acids in combinatorial synthesis. tools, equivalent to phage demonstrate, 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 is still accomplished in either scope and coverage.

Further information regarding the five quantity Set and buying info might 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))

Sample text

Soon, it became an important amino protecting group to be used along with Z group. 2 Reagents and conditions for cleavage of Na-Aloc protection. Scavengers Notes Secondary amines Piperidine, DEA, morpholine;a) 4-methylmorpholine in DCM/AcOH [90] Excess nucleophile is required to displace the equilibrium of the allyl transfer reaction towards deprotection. 1,3-Dicarbonyl compounds as nucleophiles;b) Dimedone, N,N0 -dimethylbarbituric acid [91] The liberated amine abstracts a proton from the acidic dicarbonyl compound, thus forming an ammonium derivative that is not allylated.

1 Formation of Dipeptide Impurities during the Introduction of Urethanes and Protocols to Overcome It Formation of detectable amounts of N-protected dipeptide acids (and even tripeptide acids) has been observed (a solvent system of toluene/AcOH (10: 1) efficiently differentiates Fmoc-peptide acids from Fmoc-amino acids on thinlayer chromatography (TLC)) when chloroformates such as Fmoc-Cl and Z-Cl are employed for the preparation of Na-urethane-protected amino acids. 36). The mixed anhydride intermediates are sufficiently stable in aqueous/organic reaction mixture and give rise to peptides even under Schotten–Baumann conditions.

17) [37]. Crystalline solids of Nps-amino acids are obtained as DCHA salts. The extreme acid stability of the group necessitates special precautions for handling of the free carboxylic acids. Nps groups can be selectively cleaved in the presence of acid-labile tert-butyl-based groups by using HCl or HBr in alcohol [38] or in aprotic solvents such as EtOAc or DMF [39]. The acidolytic fission of the sulfenamide bond gives rise to the free amine as well as Nps-Cl, which can cause reattachment of the group.

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