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Amino acids as CH-acids

16. Kinetic CH-acidity of Schiff bases of amino acid esters, and the synthesis of threonine and tryptophan from the ethyl ester of N-salicylideneglycine

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Bulletin of the Academy of Sciences of the USSR, Division of chemical science Aims and scope

Conclusions

  1. 1.

    A study has been made of the base catalyzed racemization of N-salicylidene-S-alanine, and of the ethyl esters of N-salicylidene-S-valine, N-salicylidene-S-alanine, N-benzylidene-S-alanine, N-o-methoxy-benzylidene-S-alanine, and N-(2-oxy-1', 5-dimethylbenzylidene)-S-alanine in methanol solutionat 25°C.

  2. 2.

    Replacement of the ionized carboxy group by a neutral carbethoxy group increases the kinetic CH-acidity of the amino acid fragment by more than four orders.

  3. 3.

    It is shown that amino acids can be synthesized from the ethyl ester of N-salicylideneglycine.

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Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1978, No. 5, pp. 1026–1033.

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Belokon', Y.N., Belikov, V.M., Maksakov, V.A. et al. Amino acids as CH-acids. Russ Chem Bull 27, 888–894 (1978). https://doi.org/10.1007/BF00928985

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  • DOI: https://doi.org/10.1007/BF00928985

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