✍ Scribed by David M. Lemaster; Frederic M. Richards
No coin nor oath required. For personal study only.
The α and β hydrogen exchange reactions catalyzed by pyridoxal have been applied to ten of the common amino acids to prepare α, β deuterated derivatives. The exchange and isolation procedure allows for numerous different samples to be processed in parallel. The deuteration at the α position range from 96 to 99% while the β deuteration levels range from 93 to 97% except for lysine (91%) which exchanges more slowly presumably due to interference of the ϵ‐amino group. The standard procedure produces approximately a gram of deuterated product for all samples except tyrosine (0.15 g) with yields from 70 to 85% using only 15 milliliters of ^2^H~2~O. The procedure has been scaled up directly to 100 millimoles for the case of alanine with virtually identical deuteration and product yield.
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## Abstract A convenient synthetic method for the preparation of α and/or β deuterium‐labelled 6‐hydroxydopamines has been developed. Nitromethane was condensed with 2,4,5‐trimethoxybenzaldehyde to give 2,4,5‐trimethoxy‐α‐nitrostyrene (__2__). The nitroethylene side chain of __2__ was reduced with