title: Synthesis and application of carbohydrate-derived morpholine amino acids.
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.
authors.affiliation: Leiden Institute of Chemistry, Gorlaeus Laboratories, P.O. Box 9502, 2300 RA Leiden, The Netherlands.
authors.forename: Gijsbert M
authors.initials: GM
authors.lastname: Grotenbreg
authors.forename: Alphert E
authors.initials: AE
authors.lastname: Christina
authors.forename: Annelies E M
authors.initials: AE
authors.lastname: Buizert
authors.forename: Gijsbert A
authors.initials: GA
authors.lastname: van der Marel
authors.forename: Herman S
authors.initials: HS
authors.lastname: Overkleeft
authors.forename: Mark
authors.initials: M
authors.lastname: Overhand
mesh_terms: D000596:Amino Acids / Q000138:chemical synthesis* / Q000737:chemistry; D002241:Carbohydrates / Q000138:chemical synthesis / Q000737:chemistry*; D008968:Molecular Conformation; D009025:Morpholines / Q000138:chemical synthesis / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000596:Amino Acids; D002241:Carbohydrates; D009025:Morpholines