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
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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
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
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