The peptide Z-Aib-Aib-Aib-L-Ala-OtBu

Acta Crystallogr C Struct Chem. 2014 Apr;70(Pt 4):405-7. doi: 10.1107/S2053229614005567. Epub 2014 Mar 21.

Abstract

The title peptide, N-benzyloxycarbonyl-α-aminoisobutyryl-α-aminoisobutyryl-α-aminoisobutyryl-L-alanine tert-butyl ester or Z-Aib-Aib-Aib-L-Ala-OtBu (Aib is α-aminoisobutyric acid, Z is benzyloxycarbonyl and OtBu indicates the tert-butyl ester), C27H42N4O7, is a left-handed helix with a right-handed conformation in the fourth residue, which is the only chiral residue. There are two 4→1 intramolecular hydrogen bonds in the structure. In the lattice, molecules are hydrogen bonded to form columns along the c axis.

Keywords: Aib-Aib-Aib-Ala; crystal structure; hydrogen bonding; left-handed helix; peptaibol antibiotic peptides; peptide; α-aminoisobutyric acid.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alanine / analogs & derivatives*
  • Alanine / chemistry*
  • Amino Acid Sequence
  • Aminoisobutyric Acids / chemistry*
  • Crystallography, X-Ray
  • Hydrogen Bonding
  • Oligopeptides / chemistry*
  • Peptides / chemistry*

Substances

  • Aminoisobutyric Acids
  • N-benzyloxycarbonyl-alpha-aminoisobutyryl-alpha-aminoisobutyryl-alpha-aminoisobutyryl-L-alanine tert-butyl ester
  • Oligopeptides
  • Peptides
  • 2-aminoisobutyric acid
  • Alanine