Solution versus solid-phase cyclization strategies for large sidechain lactam-bridged peptides: A comparative study
✍ Scribed by Julio A. Camarero; Jordi J. Cairó; Ernest Giralt; Dr David Andreu
- Publisher
- John Wiley and Sons
- Year
- 1995
- Tongue
- English
- Weight
- 724 KB
- Volume
- 1
- Category
- Article
- ISSN
- 1075-2617
No coin nor oath required. For personal study only.
✦ Synopsis
Abstract
A 22‐residue peptide with a sidechain lactam bridge involving 18 residues (60‐atom cycle) has been synthesized. Three different protection schemes using Fmoc/^t^Bu/cyclohexyl, Fmoc/^t^Bu/allyl or Boc/Bzl/ fluorenylmethyl protecting group combinations have been explored for the solid phase of the linear precursors, which have been subsequently cyclized in solution or in the solid phase. Cyclization yields in solution have been consistently better than on solid phase; however, the solid‐phase strategy requires fewer purification steps and therefore global yields are comparable.