title: Synthesis of alkylated sugar amino acids: conformationally restricted L-Xaa-L-Ser/Thr mimics.
abstract: Two synthetic strategies for the generation of delta-substituted pyranoid sugar amino acids (SAAs) are evaluated. The first employs chiral nonracemic tert-butane sulfinamides as key reagents. Regardless of the stereochemistry of the applied sulfinamide, the product formed has a stereochemistry resembling that of a d amino acid at C7. Direct Grignard reaction on formyl-tetra-O-benzyl-beta-D-C-glucopyranoside in the second strategy and subsequent Mitsunobu inversion, yields the l,l-dipeptide isosters.
authors.affiliation: Leiden Institute of Chemistry, Department of Bioorganic Synthesis, PO box 9502, 2300 RA, Leiden, The Netherlands.
authors.forename: Martijn D P
authors.initials: MD
authors.lastname: Risseeuw
authors.forename: Jaroslaw
authors.initials: J
authors.lastname: Mazurek
authors.forename: Arjan
authors.initials: A
authors.lastname: van Langenvelde
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: D000478:Alkylation; D000596:Amino Acids / Q000138:chemical synthesis / Q000737:chemistry*; D004151:Dipeptides / Q000138:chemical synthesis* / Q000737:chemistry; D012694:Serine / Q000737:chemistry*; D013237:Stereoisomerism; D013400:Sugar Acids / Q000138:chemical synthesis* / Q000737:chemistry; D013912:Threonine / Q000737:chemistry*
chemical_list: D000596:Amino Acids; D004151:Dipeptides; D013400:Sugar Acids; D013912:Threonine; D012694:Serine