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A convenient synthesis of 2S, 3S-[3-2H]-serine and 2S, 3R-[2, 3-2H2]-serine

✍ Scribed by Lawrence Slieker; Stephen J. Benkovic

Publisher
John Wiley and Sons
Year
1982
Tongue
French
Weight
380 KB
Volume
19
Category
Article
ISSN
0022-2135

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✦ Synopsis

Both 2S,3R-[2,3-2H2]-serine 5 and 2S,3S-[3-2H]-serine 6 have been pre ared from (E)-methyl-[2,3-2H2]-acrylate and (Z)-ethyl-[3-qH]-acrylate, respectively. The acrylate esters were converted to a mixture of isomeric bromohydrins by treatment with N-bromoacetamide. The ratio of 2-bromo-3-hydroxy species to the 2-hydroxy-3-bromo isomer was approximately 3:l. Conversion to the corresponding azido alcohols by treatment with NaN3 followed by catalytic reduction over Pd gave the alkyl esters of serine and isoserine. Purification and hydrolysis yielded serine in typically 20-25W yield from methyl or ethyl acrylate.

enzymatically by hog kidney acylase I treatment of the N-acetyl derivative. and the ratio of proton intensity in the diastereotopic positions at C-3 were measured to be HS/HR = 11 for 2 and HR/HS = 4.4 for 5.

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