| Autor: |
Azev, V. N., Chulin, A. N., Molchanov, M. V., Miroshnikov, A. I. |
| Předmět: |
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| Zdroj: |
Russian Journal of Bioorganic Chemistry; Jun2024, Vol. 50 Issue 3, p733-740, 8p |
| Abstrakt: |
Objective: (S)-2-{3-[(Benzyloxy)carbonyl]-5-oxooxazolidin-4-yl}acetic acid is an useful intermediate in the preparation of β-branched peptide derivatives of aspartic acid. However, we and others observed the formation of side products in the reaction of activated esters of this compound with amino acid derivatives. This suitably protected aspartic acid derivative exists as a mixture of E and Z rotamers that complicates the interpretation of NMR spectra of the products obtaind from it. Therefore, some of the failures in the preparation of β-branched aspartic acid derivatives could be due to misinterpretation of spectral data. Methods: The selectivity of the reaction of pentafluorophenyl (S)-2-{3-[(benzyloxy)carbonyl]-5-oxooxazolidin-4-yl}acetate with amino acid esters was explored with particular emphasis on the rigorous structure assignment of the products using high-temperature NMR experiments. Results and Discussion: The isomeric products of the reaction were isolated and identified. One of the isomers is an expected dipeptide, and its isomer is an N-(hydroxymethyl-amino)succinimide formed by methylene bridge cleavage. The steric bulkiness of amino acid esters favors dipeptide formation, but the reaction selectivity is quite unpredictable. Conclusions: The protection of the α-carboxyl group of aspartic acid in the form of (5-oxooxazolidin-4-yl)acetic acid derivatives has a number of limitations that must be taken into account, when this derivative is considered for use in the preparation of β-branched peptides. [ABSTRACT FROM AUTHOR] |
| Databáze: |
Complementary Index |
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