Journal
JOURNAL OF PEPTIDE RESEARCH
Volume 65, Issue 2, Pages 229-260Publisher
WILEY
DOI: 10.1111/j.1399-3011.2005.00214.x
Keywords
peptide chemistry; chemical ligation; thioligation; beta-amino acids; beta-peptide
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A brief survey of the history of peptide chemistry from Theodore Curtius to Emil Fischer to Bruce Merrifield is first presented. The discovery and development of peptide ligation, i.e. of actual chemical synthesis of proteins are described. In the main chapter, 'Synthesis of Proteins by Chemical Ligation' a detailed discussion of the principles, reactivities and mechanisms involved in the various coupling strategies now applied (ligation, chemical ligation, native chemical ligation) is given. These include coupling sites with cysteine and methionine (as well as the seleno analogs), histidine, glycine and pseudo-prolines, 'unrestricted' amino-acid residues (using the Staudinger reaction), as well as solid-phase segment coupling by thioligation of unprotected peptides. In another section, 'Synthesis of beta-peptides by Thioligation', couplings involving beta(2)- and beta(3)-peptides are described (with experimental details).
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