Synthesis of L-2,3-trans-3,4-cis-Dihydroxyproline Building Blocks for Peptide Synthesis.
L-2,3-trans-3,4-cis-N-Fluorenylmethoxycarbonyl-3,4-dihydroxy-3,4-O-isopropylidineproline (9) has been prepared from D-gulonolactone in nine steps and an overall yield of 22%. Compound 9 has been converted to its allyl ester 13. Compounds 9 and 13 were investigated as building blocks for the incorporation of dihydroxyproline into peptides, with compound 9 serving as a carboxyl component and compound 13 as a precursor to an amino component for peptide coupling reactions. Their utility was demonstrated by the synthesis of dipeptides 11 and 15.
Weir
Claudette A.
CA
Department of Chemistry, University of Auckland, Private Bag 92019, Auckland, New Zealand.
Taylor
Carol M.
CM