A series of 1,3-diamino-2-propanol derivatives have been synthesized on solid phase as potential aspar'tic acid protease irdaibitors. The developed methodology allows the incorporation of either an alkyl group or H at the R 2 site of hydroxyethylamine isostere.
Incorporation of a phosphonic acid isostere of aspartic acid into peptides using Fmoc-solid phase synthesis
✍ Scribed by P.A. Lohse; R. Felber
- Publisher
- Elsevier Science
- Year
- 1998
- Tongue
- French
- Weight
- 229 KB
- Volume
- 39
- Category
- Article
- ISSN
- 0040-4039
No coin nor oath required. For personal study only.
✦ Synopsis
A short synthesis of a novel Fmoc-derivative 2b of the phosphonic acid isostere I of aspartic acid is presented. Incorporation of 2b into peptides was readily achieved using standard Fmoc-solid phase synthesis. Efficient removal of the allyl protecting groups after sequence assembly under mild conditions using Pd(0) catalysis afforded phosphonopeptides 3a and 3b in high purity.
📜 SIMILAR VOLUMES
## Abstract The sequence‐dependent, acid‐ or base‐catalysed aspartimide formation is one of the most serious side reactions in solid‐phase synthesis of peptides containing aspartic acid. In the present work, we investigated the susceptibility of 4‐{__N__‐[1‐(4,4‐dimethyl‐2,6‐dioxocyclohexylidene)‐3