Synthesis of polymer-supported organic compounds for the preparation of amines, amino acids and peptides

Subject Areas :

Maaroof Zarei ¹ , Aliasghar Jarrahpour ² , Abdolhamid Fadavi ³

1 - Associate Prof. of Organic Chemistry, Department of Chemistry, Faculty of Sciences, University of Hormozgan, Bandar Abbas, Iran
2 - Professor of Organic Chemistry, Department of Chemistry, College of Sciences, Shiraz University, Shiraz, Iran
3 - Assistant Prof. of Chemistry-Polymer, Department of Chemistry, Marvdasht Branch, Islamic Azad University, Marvdasht, Iran

Received: 2020-12-17 Accepted : 2020-12-17 Published : 2020-09-22

Keywords: amino acid, Peptide, amine, Merrifield resin, Solid-phase synthesis,

Abstract :

Trimellitic anhydride was attached to Merrifield resin and used in the synthesis of primary amines by reaction with HMDS and conversion of anhydride moiety to phthalimide group. The resin containing phthalimide group was also used in the preparation of amino carboxylic acids. Preparation of tripeptide derived from glycine was conveniently performed by this method, too. All reactions were easily progressed and purification of products was performed using simple washing of resin without using column chromatography. The yield of products is good to excellent yield. Significantly, residual resin from reactions can be used again in the mentioned syntheses with its conversion to resin containing trimellitic anhydride. Based on the functional groups, infrared spectroscopy was used to monitoring ‎ progress of a reaction ‎and product formation. Purification using simple washing and filtering, avoidance of expensive and time-consuming separation techniques and sequential reactions are some advantages of present method.

References:

[1]  Gabriel, S.; Ber. Dtsch. Chem. Ges. 20, 2224–2236, 1887.

[2]  Gibson, M.S.; Bradshaw, R.W.; Angew. Chem. Int. Ed. Engl. 7, 919-930, 1968.

[3]  Li, J.J.; Corey, E.J.; Name Reactions for Functional Group Transformations, John Wiley & Sons, Inc. 438-450, 2007.

[4]  Ing, H.R.; Manske, R.H.F.; J. Chem. Soc. 129, 2348–2351, 1926.

[5]  Wasfy, A.F.; Aly, A.A.; Behalo, M.S.; Mohamed, N.S.; J. Heterocycl. Chem. 57, 12–25, 2020.

[6]  Wang Z.; “Comprehensive Organic Name Reactions and Reagents”, John Wiley & Sons, Inc., 2010.

[7]  Laue, T.; Plagens, A.; “Named Organic Reactions”, Second Edition, John Wiley & Sons, 2005.

[8]  Patai,S.; Patai Series: “The Amino Group”, John Wiley & Sons Ltd., New York, 1968.

[9]  Zalewski, R.I.; "Patai Series: Acid–base properties of carboxylic acids, esters and amides, The Amino Group”, John  Wiley & Sons Ltd., New York, 1992.

[10] Toda, F.; Acc. Chem. Res. 28, 480–486, 1995.

[11] Merrifield, R.B.; J. Am. Chem. Soc. 85, 2149-2154, 1963.

[12] Trias, J.; Curr. Opin. Microbiol. 4, 520-525, 2001.

[13] Dorwald, F.Z.; “Organic synthesis on Solid Phase”, Wiley-VCH Verlag GmbH: Weinheim, 2002.

[14] Wilson, S.R.; Czarnik, A.W.; “Combinatorial Chemistry, Synthesis and Application”, Wiley, New York, 1997.

[15] Rafai Far, A.; Angew. Chem. Int. Ed. 42, 2340–2348, 2003.

[16] Guillier, F.; Orain, D.; Bradley, M.; Chem. Rev. 100, 2091-2157, 2000.

[17] Farajollah, R.; Alavi Nikje, M.M.; Dorkoosh, F.A.; Vakili, M.; Journal of Applied Research in Chemistry 8 (4), 5-12, 2015.

[18] Krchnak, V.; Holladay, M.W.; Chem. Rev. 102, 61-91, 2002.

[19] Lu, J.; Toy, P.H.; Chem. Rev. 109, 815–838, 2009.

[20] Tamami, B.; Goudarzian, M.; Iran. J. Chem. Chem. Eng. (IJCCE), 15, 63-71, 1996.

[21] Salimi, H.; Rahimi, A.; Pourjavadi, A.; Monatsh. Chem. 138, 363–379, 2007.

[22] Booth, S.; Hermkens, P.H.H.; Ottenheijm, H.C.J.; Rees D.; Tetrahedron 52, 4527-4554, 1996.

[23] Merrifield, R.B.; Angew. Chem. Int. Ed. Engl. 24, 799-892, 1985.

[24] Yang, Q.; Zhang, Y.; Zeng, W.; Duan, Z.-C.; ‎Sang, X.; Wang, D.; ‎Green Chem. 21, 5683-5690, 2019. ‎

[25] Itsuno, S.; Uchikoshi, K.; Ito, K.; J. Am. Chem. Soc. 112, 8187-8188,1990.

[26] Gerigk, U.; Gerlach, M.; Neumann, W.E.; Vieler, R.; Weintritt, V.; Synthesis 1990, 448-452, 1990.

[27] Sheng, Q.; Stover, H.D.H.; Macromolecules 30, 6712-6714, 1997.

[28] Mahata, P.; Sen, D.; Natarajan, S.; Chem. Commun. 11, 1278-1280, 2008.

[29] Pramanick, D.; Pramanick, R.; Betal, G.; J. Appl. Polym. 91, 343-346‎, 2004‎.

[30] Ma, S.; Qian, J.; Zhuang, Q.; Li, X.; Kou, W.; Peng, S.;‏ J. Macromol. Sci. A Pure Appl. Chem. 55, 414-‎‎421, 2018.

[31] Mohamed, N.A.; Al-Harby, N.F.; Almarshed, M.S.; Int. J. Biol. Macromol. 132, 416-428‎, 2019.

[32] Campaigne, E.; Archer, W.L.; J. Am. Chem. Soc. 75, 989-991, 1953.

[33] Nikpour, F.; Kazemi, S.; Sheikh, D.; Heterocycles 68, 1559-1564, 2006.

[34] Kolahdoozan, M.; Razieh Mirsafae, R.; Designed Monom. Polym. 15, 289–301, 2012.

[35] Mallakpour, S.; Dehghani, M.; Synth. React. Inorg. Met.-Org. Nano-Metal. Chem. 44, 235–241, 2014.

[36] Faghihi, K.; Shabanian, M.; Bull. Chem. Soc. Ethiop. 25, 97-102, 2011.

[37] Banihashemi, A.; Tamami, B.; Abdolmaleki, A.; J. Iran. Chem. Soc. 1, 141-151, 2004.

[38] Banihashemi, A.; Behniafar, H.;‏ Polym. Int. 52, 136-1144, 2003.‎

[39] Aronov, A.M.; Gelb, M.H.; Tetrahedron Lett. 39, 4947-4950, 1998.

[40] Zarei, M.; Tetrahedron 73, 1867-1872, 2017.

[41] Zarei, M.; Chemistry Select 3, 11273–11276, 2018.

[42] Mohamadzadeh, M.; Zarei, M.; Vessal, M.; Bioorg. Chem. 95, 103515, 2020.

[43] Jarrahpour, A.; Fadavi, A.; Zarei, M.; Bull. Chem. Soc. Jpn. 84, 320-327, 2011.‎

[44] Kim, J.M.; Bogdan, M.A.; Mariano, P.S., J. Am. Chem. Soc. 115, 10591–10595, 1993.