Synthesis of alkylated sugar amino acids: conformationally restricted L-Xaa-L-Ser/Thr mimics.
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.
Risseeuw
Martijn D P
MD
Leiden Institute of Chemistry, Department of Bioorganic Synthesis, PO box 9502, 2300 RA, Leiden, The Netherlands.
Mazurek
Jaroslaw
J
van Langenvelde
Arjan
A
van der Marel
Gijsbert A
GA
Overkleeft
Herman S
HS
Overhand
Mark
M
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*
D000596:Amino Acids; D004151:Dipeptides; D013400:Sugar Acids; D013912:Threonine; D012694:Serine