1. Synthesis and structure of cyclic phosphopeptides containing a phosphodiester linkage
- Author
-
van Oijen, Anita H., Behrens, Stefan, Mierke, Dale F., Kessler, Horst, van Boom, Jacques H., and Liskamp, Rob M.J.
- Subjects
Cyclic compounds -- Research ,Peptides -- Research ,Molecular structure -- Research ,Organic compounds -- Synthesis ,Biological sciences ,Chemistry - Abstract
Three cyclic phosphopeptides containing intramolecular phosphodiester linkages were synthesized. Precursors for the macrocyclization by phosphitylation were synthesized using Boc-L-Ser(OBn)-OH or Boc-L-Thr(OBn)-OH as starting materials. The cyclic phosphopeptides were then generated after phosphitylation with 4-chlorobenzyl bis(N, N-diisopropylamino)phosphinite or 4-chlorobenzyl dichlorophoshinite, oxidation and hydrogenolysis. Nuclear magnetic resonance spectroscopy and molecular dynamics simulations were used to determine the structure of one of the cyclic phosphopeptides in solution.
- Published
- 1993