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

By Andrew B. Hughes

ISBN-10: 3527321039

ISBN-13: 9783527321032

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 can be the single sequence to hide this crucial subject in natural and biochemistry. Drawing upon the mixed services of the foreign "who's who" in amino acid learn, those volumes symbolize a true benchmark for amino acid chemistry, offering a complete dialogue of the prevalence, 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 via the inclusion of experimental procedures.


The five volumes hide the subsequent topics:

Volume 1: Origins and Synthesis of Amino Acids

Volume 2: transformed Amino Acids, Organocatalysis and Enzymes

Volume three: construction 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 established in 3 major sections. the 1st part is set safety reactions and amino acid dependent peptidomimetics. the second one, and so much huge, half is dedicated to the medicinal chemistry of amino acids. It comprises, between others, the chemistry of alpha- and beta amino acids, peptide medicines, and advances in N- and O-glycopeptide synthesis. the ultimate half offers with amino acids in combinatorial synthesis. equipment, reminiscent of 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 is still accomplished in either scope and coverage.

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

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Extra resources 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

2 One-Pot Na Protection and Ca Activation The two key reactions in peptide synthesis, Na protection and a-carboxy activation, can be executed in a single pot when pentafluorophenyl carbonates such as 9fluorenylmethylpentafluorophenylcarboante (Fmoc-OPfp) are employed as urethane donors. Na-Fmoc-amino acid pentafluorophenyl esters can be directly obtained by in situ esterification of the pentafluorophenol (liberated during acylation of the a-amino group by Fmoc-OPfp) by the addition of N,N0 -dicyclohexylcarbodiimide (DCC) to the reaction mixture after the formation of Na-Fmoc-amino acids [138].

The mechanism of acidolytic cleavage is shifted towards the SN2 pathway by these substituents. The electron-releasing substituents (X ¼ OMe (46) or Me (47)) increase the acid lability of the groups by offering higher resonance stabilization to the benzyl cation formed during cleavage [55, 56]. Deblocking preferentially occurs through an SN1 pathway. In terms of hydrogenolytic cleavage of 43, 45, and 48, a deviation from the standard mode of alkyl-oxygen bond fragmentation is observed. 25) [57].

18 Cleavage of the Na-Nps group. not possible in aprotic solvent. In this case an additional equivalent of HCl is added to protect the deblocked amine as its hydrochloride salt. Scavengers such as 2-methyl indole and 1-acetyl tryptophan are added to decrease the activity of the hydrogen halide in alcohol, and thus protect other acid-labile groups. 18). 2 Urethanes (Carbamates or Alkyloxycarbonyl Groups) In 1932, Bergmann and Zervas introduced the benzyloxycarbonyl (Cbz or Z) group as a new amino protecting group [40].

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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)) by Andrew B. Hughes

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