Derivatives of (5-Oxooxazolidin-4-yl)acetic acids in aspartic acid α-carboxyl protection: a word of caution
- Authors: Azev V.N.1, Chulin A.N.1, Molchanov M.V.2, Miroshnikov A.I.3
-
Affiliations:
- Branch of Shemyakin–Ovchinnikov Bioorganic Chemistry Institute RAS
- Istitute for Theoretical and Experimental Biophysics RAS
- Shemyakin–Ovchinnikov Bioorganic Chemistry Institute RAS
- Issue: Vol 50, No 3 (2024)
- Pages: 295-300
- Section: Articles
- URL: https://journals.rcsi.science/0132-3423/article/view/261478
- DOI: https://doi.org/10.31857/S0132342324030084
- EDN: https://elibrary.ru/NZIGZT
- ID: 261478
Cite item
Open Access
Access granted
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.
Full Text
About the authors
V. N. Azev
Branch of Shemyakin–Ovchinnikov Bioorganic Chemistry Institute RAS
Author for correspondence.
Email: viatcheslav.azev@bibch.ru
Russian Federation, prosp. Nauki 6, Puschino, 142290
A. N. Chulin
Branch of Shemyakin–Ovchinnikov Bioorganic Chemistry Institute RAS
Email: viatcheslav.azev@bibch.ru
Russian Federation, prosp. Nauki 6, Puschino, 142290
M. V. Molchanov
Istitute for Theoretical and Experimental Biophysics RAS
Email: viatcheslav.azev@bibch.ru
Russian Federation, Institutskaya ul. 3, Puschino, 142290
A. I. Miroshnikov
Shemyakin–Ovchinnikov Bioorganic Chemistry Institute RAS
Email: viatcheslav.azev@bibch.ru
Russian Federation, ul. Miklukho-Maklaya 16/10, Moscow, 117997
References
- Itoh M.I. // Chem. Pharm. Bull. 1969. V. 17. P. 1679– 1686. https://doi.org/10.1248/cpb.17.1679s
- Scholtz J.M., Bartlett P.A. // Synthesis. 1989. P. 542– 544. https://doi.org/10.1055/s-1989-27311
- Mehrotra A.P., Webster K.L., Gani D. // J. Chem. Soc., Perkin Trans. 1. 1997. P. 2495–2512. https://doi.org/10.1039/A702407J
- 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
- 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
- Subirós-Funosas R., El-Faham A., Albericio F. // Tetrahedron. 2011. V. 45. P. 8595–8606. https://doi.org/10.1016/j.tet.2011.08.046
- Benassi R., Folli U., Schenetti L., Taddei F. // Adv. Het. Chem. 1987. V. 41. P. 75–186. https://doi.org/10.1016/S0065-2725(08)60161-0
- Tillett J.G. // Chem. Rev. 1976. V. 76. P. 747–772. https://doi.org/10.1021/cr60304a004
- Armarego W.L.F., Chai C. // Purification of Laboratory Chemicals, 6th ed. Oxford: Butterworth-Heinemann, 2012.
Supplementary files
