Synthesis and application of carbohydrate-derived morpholine amino acids

Gijsbert M Grotenbreg; Alphert E Christina; Annelies E M Buizert; Gijsbert A van der Marel; Herman S Overkleeft; Mark Overhand

doi:10.1021/jo048630x

Synthesis and application of carbohydrate-derived morpholine amino acids

J Org Chem. 2004 Nov 26;69(24):8331-9. doi: 10.1021/jo048630x.

Authors

Gijsbert M Grotenbreg¹, Alphert E Christina, Annelies E M Buizert, Gijsbert A van der Marel, Herman S Overkleeft, Mark Overhand

Affiliation

¹ Leiden Institute of Chemistry, Gorlaeus Laboratories, P.O. Box 9502, 2300 RA Leiden, The Netherlands.

PMID: 15549804
DOI: 10.1021/jo048630x

Abstract

The synthesis of series of diversely functionalized epsilon-morpholine amino acids (MAAs, 5a-h) starting from an epsilon-sugar amino acid and following a two-step oxidative glycol cleavage/reductive amination strategy, is described. In an alternative synthetic scheme, diastereoisomerically pure delta-MAAs (12a,b) were obtained. Oligopeptides containing MAAs were prepared either by direct incorporation of a MAA building block or by subjecting a fully assembled SAA-containing peptide to the two-step glycol cleavage/reductive amination procedure.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Amino Acids / chemical synthesis*
Amino Acids / chemistry
Carbohydrates / chemical synthesis
Carbohydrates / chemistry*
Molecular Conformation
Morpholines / chemical synthesis
Morpholines / chemistry*
Stereoisomerism

Substances

Amino Acids
Carbohydrates
Morpholines