Nsc and FmocNα-amino protection for solid-phase peptide synthesis: a parallel study
- 1 August 2000
- journal article
- research article
- Published by Wiley in Chemical Biology & Drug Design
- Vol. 56 (2) , 63-69
- https://doi.org/10.1034/j.1399-3011.2000.00711.x
Abstract
The 2‐(4‐nitrophenylsulfonyl)ethoxycarbonyl (Nsc) group is an alternative to Fmoc for Nα‐protection in solid‐phase peptide synthesis. Nsc‐amino acids may be particularly suitable for automatic synthesizers, in which the amino acids are stored in solution, and the incorporation of residues prone to racemization such as Cys and His. Owing to the hydrophilicity of the Nsc group, these derivatives are useful for the preparation of protected peptides in convergent solid‐phase peptide synthesis strategies.Keywords
This publication has 19 references indexed in Scilit:
- Amino-Protecting Groups Subject to Deblocking under Conditions of Nucleophilic Addition to a Michael Acceptor. Structure−Reactivity Studies and Use of the 2-(tert-Butylsulfonyl)-2-propenyloxycarbonyl (Bspoc) GroupThe Journal of Organic Chemistry, 1999
- The 1,1-Dioxobenzo[b]thiophene-2-ylmethyloxycarbonyl (Bsmoc) Amino-Protecting GroupThe Journal of Organic Chemistry, 1999
- Coupling Difficulty Associated with Interchain Clustering and Phase Transition in Solid Phase Peptide SynthesisJournal of the American Chemical Society, 1995
- Redox‐active bis‐cysteinyl peptides. I. Synthesis of cyclic cystinyl peptides by conventional methods in solution and on solid supportsBiopolymers, 1994
- 2-(4-nitrophenyl)sulfonylethoxycarbonyl (Nsc) group as a base-labile α-amino protection for solid phase peptide synthesisTetrahedron Letters, 1994
- Use of polar picolyl protecting groups in peptide synthesisThe Journal of Organic Chemistry, 1988
- Methodological implications of simultaneous solid-phase peptide synthesis. 1. Comparison of different coupling proceduresThe Journal of Organic Chemistry, 1988
- New base‐labile amino‐protective groups for peptide synthesisRecueil des Travaux Chimiques des Pays-Bas, 1988
- A new amino protecting group removable by reduction. Chemistry of the dithiasuccinoyl (Dts) functionJournal of the American Chemical Society, 1977
- Solvation of the polymer matrix. Source of truncated and failure sequences in solid phase synthesisThe Journal of Organic Chemistry, 1973