A practical synthesis of N α-Fmoc protected L-threo-ß-hydroxyaspartic acid derivatives for coupling via α- or ß-carboxylic group.
Amino Acids
; 42(1): 285-93, 2012 Jan.
Article
em En
| MEDLINE
| ID: mdl-21082204
ABSTRACT
A simple and practical general synthetic protocol towards orthogonally protected tHyAsp derivatives fully compatible with Fmoc solid-phase peptide synthetic methodology is reported. Our approach includes enantioresolution of commercially available D ,L -tHyAsp racemic mixture by co-crystallization with L -Lys, followed by ion exchange chromatography yielding enantiomerically pure L -tHyAsp and D -tHyAsp, and their selective orthogonal protection. In this way N ( α )-Fmoc protected tHyAsp derivatives were prepared ready for couplings via either α- or ß-carboxylic group onto the resins or the growing peptide chain. In addition, coupling of tHyAsp via ß-carboxylic group onto amino resins allows preparation of peptides containing tHyAsn sequences, further increasing the synthetic utility of prepared tHyAsp derivatives.
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Coleções:
01-internacional
Base de dados:
MEDLINE
Tipo de estudo:
Guideline
Idioma:
En
Ano de publicação:
2012
Tipo de documento:
Article