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Letters in Organic Chemistry

Editor-in-Chief

ISSN (Print): 1570-1786
ISSN (Online): 1875-6255

Research Article

Diethylphosphoryl-OxymaB (DEPO-B) as a Solid Coupling Reagent for Amide Bond Formation

Author(s): Ashish Kumar, Yahya E. Jad, Ayman El-Faham, Beatriz G. de la Torre* and Fernando Albericio*

Volume 16, Issue 1, 2019

Page: [30 - 33] Pages: 4

DOI: 10.2174/1570178615666180612074420

Price: $65

Abstract

A new phosphonium based coupling reagent DEPO-B has been synthesized from 5- (hydroxyimino)-1,3-dimethylpyrimidine-2,4,6 (1H,3H,5H)-trione (Oxyma B) and diethyl chlorophosphate in presence of base. It is a solid material and the hydrolytic stability and solubility was evaluated for confirming its capability for usage in automated peptide synthesizer.

Keywords: Coupling reagent, phosphonium salts, diethylphosphoryl-OxymaB, hydrolytic stability, solubility.

Graphical Abstract
[1]
El-Faham, A.; Albericio, F. Chem. Rev., 2011, 111(11), 6557-6602.
[2]
Al-Warhi, T.I.; Al-Hazimi, H.M.; El-Faham, A. J. Saudi Chem. Soc., 2012, 16(2), 97-116.
[3]
Valeur, E.; Bradley, M. Chem. Soc. Rev., 2009, 38(2), 606-631.
[4]
Fan, C-X.; Hao, X-L.; Ye, Y-H. Synth. Commun., 1996, 26(7), 1455-1460.
[5]
Li, H.; Jiang, X.; Ye, Y-h.; Fan, C.; Romoff, T.; Goodman, M. Org. Lett., 1999, 1(1), 91-94.
[6]
Shioiri, T.; Ninomiya, K.; Yamada, S. J. Am. Chem. Soc., 1972, 94(17), 6203-6205.
[7]
Ninomiya, K.; Shioiri, T.; Yamada, S-I. Tetrahedron, 1974, 30(14), 2151-2157.
[8]
Brady, S.F.; Varga, S.L.; Freidinger, R.M.; Schwenk, D.A.; Mendlowski, M.; Holly, F.W.; Veber, D.F. J. Org. Chem., 1979, 44(18), 3101-3105.
[9]
Davies, J.S. J. Pept. Sci., 2003, 9(8), 471-501.
[10]
Trost, B.M. Angew. Chem. Int. Ed., 1995, 34(3), 259-281.
[11]
Ye, Y.h.; Li, H.; Jiang, X. Pept. Sci., 2005, 80(2-3), 172-178.
[12]
Albericio, F.; Bofill, J.M.; El-Faham, A.; Kates, S.A. J. Org. Chem., 1998, 63(26), 9678-9683.
[13]
El-Faham, A.; Albericio, F. J. Pept. Sci., 2010, 16(1), 6-9.
[14]
Subirós-Funosas, R.; Prohens, R.; Barbas, R.; El-Faham, A.; Albericio, F. Chem. Eur. J., 2009, 15(37), 9394-9403.
[15]
Mitachi, K.; Kurosu, Y.E.; Hazlett, B.T.; Kurosu, M. J. Pept. Sci., 2016, 22(3), 186-191.
[16]
Wang, Q.; Wang, Y.; Kurosu, M. Org. Lett., 2012, 14(13), 3372-3375.
[17]
Jad, Y.E.; Acosta, G.A.; Govender, T.; Kruger, H.G.; El-Faham, A.; de la Torre, B.G.; Albericio, F. ACS Sustain. Chem.& Eng., 2016, 4(12), 6809-6814.
[18]
Kumar, A.; Jad, Y.E.; de la Torre, B.G.; El-Faham, A.; Albericio, F. J. Pept. Sci., 2017, 23(10), 763-768.
[19]
Kumar, A.; Jad, Y.E.; El-Faham, A.; Albericio, F. Tetrahedron Lett., 2017, 58(30), 2986-2988.
[20]
Jad, Y.E.; Acosta, G.A.; Khattab, S.N.; de la Torre, B.G.; Govender, T.; Kruger, H.G.; El-Faham, A.; Albericio, F. Amino Acids, 2016, 48(2), 419-426.

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