Synthesis and application of carbohydrate-derived morpholine amino acids |
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| Authors: | Grotenbreg Gijsbert M Christina Alphert E Buizert Annelies E M van der Marel Gijsbert A Overkleeft Herman S Overhand Mark |
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| Institution: | Leiden Institute of Chemistry, Gorlaeus Laboratories, P.O. Box 9502, 2300 RA Leiden, The Netherlands. |
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| 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. |
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