Email this article Synthesis of glycyl-(S)-5-hydroxynorvaline
- Authors: Chulakov E.N.1, Tumashov A.A.1, Gruzdev D.A.1, Levit G.L.1, Krasnov V.P.1
-
Affiliations:
- Postovsky Institute of Organic Synthesis, Ural Branch, Russian Academy of Sciences
- Issue: Vol 59, No 11 (2023)
- Pages: 1507-1512
- Section: Articles
- URL: https://ogarev-online.ru/0514-7492/article/view/247269
- DOI: https://doi.org/10.31857/S0514749223110149
- EDN: https://elibrary.ru/NDGSMP
- ID: 247269
Cite item
Full Text
Abstract
The dipeptide glycyl-( S )-5-hydroxynorvaline was obtained from 1- tert -butyl 5-methyl N -Boc-glycyl-( S )-glutamate as a result of saponification and subsequent reduction of the activated 5-carboxyl group with sodium borohydride followed by removal of the N -Boc and OBu t protecting groups by refluxing in a dioxane-water mixture. Using the example of the synthesis of ( S )-5-hydroxynorvaline, it has been shown that the used sequence of chemical transformations is not accompanied by racemization.
Keywords
About the authors
E. N. Chulakov
Postovsky Institute of Organic Synthesis, Ural Branch, Russian Academy of Sciences
Email: chulakov@ios.uran.ru
A. A. Tumashov
Postovsky Institute of Organic Synthesis, Ural Branch, Russian Academy of Sciences
D. A. Gruzdev
Postovsky Institute of Organic Synthesis, Ural Branch, Russian Academy of Sciences
G. L. Levit
Postovsky Institute of Organic Synthesis, Ural Branch, Russian Academy of Sciences
V. P. Krasnov
Postovsky Institute of Organic Synthesis, Ural Branch, Russian Academy of Sciences
References
- Carmo-Silva A.E., Keys A.J., Beale M.H., Ward J.L., Baker J.M., Hawkins N.D., Arrabaça M.C., Parry M.A.J. Phytochemistry. 2009, 70, 664-671. doi: 10.1016/j.phytochem.2009.03.001
- Yan J., Lipka A.E., Schmelz E.A., Buckler E.S., Jander G. J. Exp. Bot. 2015, 66, 593-602. doi: 10.1093/jxb/eru385
- Ayala A., Cutler R.G. Free Radical Biol. Med. 1996, 21, 65-80. doi: 10.1016/0891-5849(95)02220-1
- Hannachi J.-C., Vidal J., Mulatier J.-C., Collet A. J. Org. Chem. 2004, 69, 2367-2373. doi: 10.1021/jo035700b
- Elbatrawi Y.M., Kang C.W., Del Valle J.R. Org. Lett. 2018, 20, 2707-2710. doi: 10.1021/acs.orglett.8b00912
- Krasnov V.P., Levit G.L., Musiyak V.V., Gruzdev D.A., Charushin V.N. Pure Appl. Chem. 2020, 92, 1277-1295. doi: 10.1515/pac-2019-1214
- Olsen R.K., Ramasamy K., Emery T. J. Org. Chem. 1984, 49, 3527-3534. doi: 10.1021/jo00193a016
- García M., Serra A., Rubiralta M., Diez A., Segarra V., Lozoya E., Ryder H., Palacios J.M. Tetrahedron Asymmetry. 2000, 11, 991-994. doi: 10.1016/S0957-4166(00)00020-3
- Wang L., Zha Z., Qu W., Qiao H., Lieberman B.P., Plössl K., Kung H.F. Nucl. Med. Biol. 2012, 39, 933-943. doi: 10.1016/j.nucmedbio.2012.03.007
- Longobardo L., Cecere N., DellaGreca M., de Paola I. Amino Acids. 2013, 44, 443-448. doi: 10.1007/s00726-012-1352-5
- Muetterties C., Janiga A., Huynh K.T., Pisano M.G., Tripp V.T., Young D.D., Poutsma J.C. Int. J. Mass Spectrom. 2014, 369, 71-80. doi: 10.1016/j.ijms.2014.06.010
- Wang J., Liang Y.-L., Qu J. Chem. Commun. 2009, 5144-5146. doi: 10.1039/b910239f
- Zinelaabidine C., Souad O., Zoubir J., Malika B., Nour-Eddine A. Int. J. Chem. 2012, 4, 73-79. doi: 10.5539/ijc.v4n3p73
- Khelili S., de Tullio P., Lebrun P., Fillet M., Antoine M.-H., Ouedraogo R., Dupont L., Fontaine J., Felekidis A., Leclerc G., Delarge J., Pirotte B. Bioorg. Med. Chem. 1999, 7, 1513-1520. doi: 10.1016/S0968-0896(99)00082-6
- Груздев Д.А., Левит Г.Л., Ольшевская В.А., Краснов В.П. ЖОрХ. 2017, 53, 756-762.
- Gruzdev D.A., Levit G.L., Ol'shevskaya V.A., Krasnov V.P. Russ. J. Org. Chem. 2017, 53, 769-776. doi: 10.1134/S1070428017050190
- Barlos K., Mamos P., Papaioannou D., Patrianakou S. J. Chem. Soc., Chem. Commun. 1987, 1583-1584. doi: 10.1039/C39870001583
Supplementary files
