Derivatives of (5-Oxooxazolidin-4-yl)acetic acids in aspartic acid α-carboxyl protection: a word of caution-Reference-Cited by-同舟云学术

Derivatives of (5-Oxooxazolidin-4-yl)acetic acids in aspartic acid α-carboxyl protection: a word of caution

Published:2024-08-11 Issue:3 Volume:50 Page:295-300
ISSN:1998-2860
Container-title:Биоорганическая химия
language:
Short-container-title:RUBI

Author:

Azev V. N.¹,Chulin A. N.¹,Molchanov M. V.²,Miroshnikov A. I.³

Affiliation:

1. Branch of Shemyakin–Ovchinnikov Bioorganic Chemistry Institute RAS

2. Istitute for Theoretical and Experimental Biophysics RAS

3. Shemyakin–Ovchinnikov Bioorganic Chemistry Institute RAS

Abstract

Isomeric products could be isolated in a reaction of pentafluorophenyl ester of (S)-2-(3-((benzyloxy)-carbonyl)-5-oxooxazolidin-4-yl)acetic acid with aminoacid esters. One product is an expected dipeptide, the isomeric one is an N-hydroxymethylamino succinimide – a product of methylene bridge cleavavge. Steric bulkness of aminoacid esters favors the formation of a peptide, however the reaction selectivity is quite unpredicatable. Moreover, the precise structure assignement requires high-temperature NMR experiments.

Publisher

The Russian Academy of Sciences

Reference9 articles.

1. Itoh M.I. // Chem. Pharm. Bull. 1969. V. 17. P. 1679– 1686. https://doi.org/10.1248/cpb.17.1679s

2. Scholtz J.M., Bartlett P.A. // Synthesis. 1989. P. 542– 544. https://doi.org/10.1055/s-1989-27311

3. Mehrotra A.P., Webster K.L., Gani D. // J. Chem. Soc., Perkin Trans. 1. 1997. P. 2495–2512. https://doi.org/10.1039/A702407J

4. Abell A.D., Edwards R.A., Oldham M.D. // J. Chem. Soc., Perkin Trans. 1. 1997. P. 1655–1662. https://doi.org/10.1039/A608165G

5. Azev V.N., Baidakova L.K., Chulin A.N., Tuzikov A.B., Kislitsyn P.G., Molchanov M.V., Miroshnikov A.I. // Russ. J. Bioorg. Chem. 2023. V. 49. P. 775–784. https://doi.org/10.1134/S1068162023040052