Aza-Amino Acid Scan for Rapid Identification of Secondary Structure Based on the Application of N-Boc-Aza1-Dipeptides in Peptide Synthesis
- 7 May 2004
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 126 (21) , 6759-6764
- https://doi.org/10.1021/ja039643f
Abstract
Azapeptides, peptide analogues in which the α-carbon of one or more of the amino acid residues is replaced with a nitrogen atom, exhibit propensity for adopting β-turn conformations. A general protocol for the synthesis of azapeptides without racemization on solid phase has now been developed by introducing the aza-amino acid residue as an N-Boc-aza1-dipeptide. This approach has been validated by the synthesis of six N-Boc-aza1-dipeptides and their subsequent introduction into analogues of the C-terminal peptide fragment of the human calcitonin gene-related peptide (hCGRP). By performing an aza-amino acid scan of such antagonist peptides, a set of aza-hCGRP analogues was synthesized to examine the relationship between turn secondary structure and biological activity.Keywords
This publication has 57 references indexed in Scilit:
- Inhibition of trypsin by t-Butyloxycarbonyl-α-aza-(4-aminophenyl)alanine phenyl esterJournal of Chemical Technology & Biotechnology, 2007
- The energetically favorable cis peptide bond for the azaglycine-containing peptide: For-AzGly-NH2 modelPhysical Chemistry Chemical Physics, 2001
- Conformational Analysis of Reverse-Turn Constraints by N-Methylation and N-Hydroxylation of Amide Bonds in Peptides and Non-Peptide MimeticsJournal of the American Chemical Society, 1998
- Site-Selective N-Methylation of Peptides on Solid SupportJournal of the American Chemical Society, 1997
- Synthesis and evaluation of diacylhydrazines as inhibitors of the interleukin-1β converting enzyme (ICE)Bioorganic & Medicinal Chemistry Letters, 1995
- Cysteine protease inhibition by azapeptide estersJournal of Medicinal Chemistry, 1992
- Synthesis of angiotensin II analogs by incorporating .beta.-homotyrosine or .beta.-homoisoleucine residuesJournal of Medicinal Chemistry, 1979
- Hydrazinverbindungen als Heterobestandteile in Peptiden. XVI. Synthese von 9‐Hydrazinoessigsäure‐, 9‐Azaglycin‐ und 5‐α‐Azaasparagin‐OxytocinJournal für Praktische Chemie, 1972
- N- [2-Isopropyl-3-(L-aspartyl-L-arginyl)-carbazoyl]-L- tyrosyl-L-valyl-L-histidyl-L-prolyl-L-phenylalanine,1 an Isostere of Bovine Angiotensin IIJournal of the American Chemical Society, 1963
- Central Stimulants. Chemistry and Structure-Activity Relationship of Aralkyl HydrazinesJournal of the American Chemical Society, 1959