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Authored by two internationally recognized experts with an excellent track record, this much-needed reference summarizes latest research in the rapidly developing field of stereoselective synthesis of enantiomerically enriched amino acids, particularly of non-proteinogenic origin. It highlights several different catalytic and stoichiometric asymmetric methods for their synthesis and also provides information on origin, biological properties, different synthetic strategies and important applications in medicine and pharmacology. Essential reading for synthetic chemists working in the field of asymmetric synthesis, natural products and peptide synthesis, stereochemistry, medicinal chemistry, biochemistry, pharmacology, and biotechnology.
(25.35) -[3-2Hi]-, (2S,3R)-C2,3-2H2]-, (2S,3S,4RS)- [3-2Hi , 4-3Hi ,U-14C]-, and (2S,3R,4RS)-[2,3-2H2, 4-3H,, U-'4C]-Glutamic acids have been synthesised and the chirality at the C-3 position proven by degradation. (2S,3S,4RS)-C3-2H,, 4-3H,,U-1*C]- and (2S,3R,4RS)- [2,3-2H2j 4-3Hi, U-14C3-Glutamic acids were used as substrates for an enzyme system comprising glutamate mutase and B-methylaspartase. A high proportion of the tritium label was lost to the medium during the enzymic incubations. The amount of tritium lost depended on the configuration at position C-3. Some possible explanations for this observation are suggested. (25.35) -C 2,3-2H2]-Asparagine has been synthesised as a precursor for the synthesis of stereo specifically deuterated tetrahydrofolic acid. Synthesis of (2S,3R)-[3-2Hi]-serine has been investigated. In one attempted route, via rearrangement of a mixed peranhydride, racemisation at the C-3 position was observed. This result was contrary to that expected from the literature on tertiary and quaternery chiral centres and mechanistic implications are discussed.
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