Synthesis and Characterisation of a Hydrophilic Support for Solid Phase Organic Reactions.

K.C. Rohini¹ , V.D. John² , K.P. Subhashchandran³

1. Christ College, University of Calicut, Calicut, India.
2. Christ College, University of Calicut, Calicut, India.
3. Sri Vyasa NSS College, University of Calicut, Calicut, India.

Correspondence should be addressed to: rohinichndrn@gmail.com.

Section:Research Paper, Product Type: Isroset-Journal
Vol.4 , Issue.3 , pp.4-7, Jun-2017

Online published on Jun 30, 2017

Copyright © K.C. Rohini, V.D. John, K.P. Subhashchandran . This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
 

View this paper at   Google Scholar | DPI Digital Library

XML View     PDF Download

How to Cite this Paper

288 Views    252 Downloads    149 Downloads

Abstract :
Glycerol dimethacrylate cross-linked 4-vinyl pyridine (GDMA-4-VP) support with optimum hydrophobic-hydrophilic balance has been introduced as a new class of polymer support in manual solid phase organic synthesis. The synthesis of GDMA-4-VP resin is based on the crosslinking of GDMA with 4-VP (in various cross linking densities) using free radical polymerization, affording a polymer containing secondary hydroxyl groups in great yield and purity. Benzoyl peroxide was used as initiator for the synthesis of polymer either via bulk polymerization or via suspension polymerization in polyvinyl alcohol, the latter yielding a beaded resin. Characterization was done by SEM and FT-IR spectroscopic techniques. The resin was found to undergo good swelling in various solvents, polar and non- polar. The synthetic utility of GDMA-4-VP resin was demonstrated by preparing biologically active Angiotensin II. The purity of the peptide was checked by HPLC.

Key-Words / Index Term :
Solid phase synthesis, GDMA-4VP resin, suspension polymerization

References :
[1]. F. Albericio ,F. G.Martin, “ Solid supports for the synthesis of peptides. From the first resin used to the most sophisticated in the market”,Chimica oggi,vol .26, Issue.4,pp.29-34,2008.
[2]. P.C.Hodge ,D.CSherrington,”Polymer supported reactions in Organic Chemistry”,Wiley:Chichester,1998.
[3]. M.Medal,”Solid phase peptide synthesis;Fields G.Ed,Academi press:New York, pp.83-104,1997.
[4]. S.Zalipzky,J.L.Chang,F.Albercio and G.Barany,React.polym.,22,243,1994.
[5]. H.Hellerman,H.W.Lucas,J.maul,V.N.R.pillai, M.Mutter, “Poly(ethylene glycol)s grafted onto cross-linked polystyrenes,2 multidetachably anchored polymer systems for the synthesis of solubilised peprtides”, Macromolecular Chemistry and Physics”Vol.184,Issue12,pp.2603-2617,1983.
[6]. R.C.Sheppered,Peptides 1971,Proc.of the 11 th Europ.pept.Symp,Nesvadba H,Eds,`3vfc j3jNorth Holland,Amsterdam 1973.
[7]. E.L.Boulpaep,W.F. Boron,” Medical Physiology: a Cellular and Molecular Approach”, St. Louis, Mo: Elsevier Saunders. pp. 771,2005.
[8]. N. Basso , N.A.Terragno, "History about the discovery of the renin-angiotensin system". Hypertension,Vol38, Issue6,pp1246–9,2001.
[9]. E. Atherton,R.C. Shepard, "Solid Phase Peptide Synthesis- A Practical Approach using the Fmoc-Polyamide Techinique" IRL Press, Oxford, 1984.
[10]. M.Bodanszky, "Principles of Peptide Synthesis", Springer Verlag: New York, 1984.
[11]. B. Merrifield,”Solid phase synthesis”, Science 232, pp.341-347,1986.