Synthesis and Application of Carbohydrate-Derived Morpholine Amino Acids
- 1 November 2004
- journal article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 69 (24) , 8331-8339
- https://doi.org/10.1021/jo048630x
Abstract
The synthesis of series of diversely functionalized ε-morpholine amino acids (MAAs, 5a−h) starting from an ε-sugar amino acid and following a two-step oxidative glycol cleavage/reductive amination strategy, is described. In an alternative synthetic scheme, diastereoisomerically pure δ-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.Keywords
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