Efficient microwave-assisted synthesis of human islet amyloid polypeptide designed to facilitate the specific incorporation of labeled amino acids

Org Lett. 2010 Nov 5;12(21):4848-51. doi: 10.1021/ol101981b.

Abstract

A cost-efficient, time-reducing solid-phase synthesis of the amyloidogenic, 37 residue islet amyloid polypeptide (IAPP) is developed using two pseudoprolines (highlighted blue in sequence) in combination with microwave technology. A yield twice that obtained with conventional syntheses is realized. The utility of this protocol is demonstrated by the synthesis of a (13)C(18)O-labeled Ser-20 IAPP variant, a prohibitively expensive and chemically challenging site to label via other protocols. TEM analysis shows the peptide forms normal amyloid (abstract image).

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Amino Acid Sequence
  • Amino Acids / chemistry*
  • Humans
  • Islet Amyloid Polypeptide / chemical synthesis*
  • Islet Amyloid Polypeptide / ultrastructure
  • Microscopy, Electron, Transmission
  • Microwaves
  • Molecular Sequence Data

Substances

  • Amino Acids
  • Islet Amyloid Polypeptide