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DOI: 10.1055/s-0029-1217715
Easy Silica Gel Supported Desymmetrization of PEG
Publikationsverlauf
Publikationsdatum:
31. Juli 2009 (online)

Abstract
Our work shows how poly(ethylene glycol), differentially functionalized at two ends, can be easily and efficiently synthesized from commercial symmetric dihydroxy PEG 600. First, we linked the polymer onto functionalized silica gel using one of its hydroxy ends. Then, the second hydroxy group was modified, and finally, the desymmetrized PEG was cleaved from the solid support.
Key words
desymmetrization - mono protection - poly(ethylene glycol) polymer - solid phase
- 1
Harris JM. In Poly(ethylene glycol) Chemistry: Biotechnical and Biomedical ApplicationsHarris JM. Plenum Press; New York: 1992. - 2
Powell GM. In Polyethylene Glycol. Handbook of Water Soluble Gums and ResinsDavison RL. McGraw-Hill; New York: 1980. p.18-21 - 3
Dreborg S.Akerblom EB. Crit. Rev. Ther. Drug Carrier Syst. 1990, 6: 315 - 4
Yamaoka T.Tabata Y.Ikada Y. J. Pharm. Sci. 1994, 83: 601 - 5
Zalipsky S. Adv. Drug. Deliv. Rev. 1995, 16: 157 - 6
Zalipsky S. Bioconjug. Chem. 1995, 6: 150 - 7
Luxon BA.Grace M.Brassard D.Broders R. Clin. Ther. 2002, 24: 1363 - 8
Roberts MJ.Bently MD.Harris JM. Adv. Drug Delivery Rev. 2002, 54: 459 - 9
Bruckdorfer T. Eur. Biopharm. Rev. 2008, Spring: 96 - 10
Yokoyama M.Okano T.Sakurai Y.Kikuchi A.Ohsako N.Nagasaki Y.Kataoka K. Bioconjugate Chem. 1992, 3: 275 - 11
Akiyama Y.Otsuka H.Nagasaki Y.Kato M.Kataoka K. Bioconjugate Chem. 2000, 11: 947 - 12
Bettinger T.Remy J.-S.Erbacher P.Behr J.-P. Bioconjugate Chem. 1998, 9: 842 - 13
Buckmann AF.Morr M.Kula M.-R. Biotechnol. Appl. Biochem. 1987, 9: 258 - 14
Zalipsky S.Albericio F.Slomenzynska U.Barany G. Int. J. Pept. Protein Res. 1987, 30: 740 - 15
Nagasaky Y.Iijima M.Kato M.Kataoka K. Bioconjugate Chem. 1995, 6: 702 - 16
Nakamura T.Nagasaki Y.Kataoka K. Bioconjugate Chem. 1998, 9: 300 - 17
Zhang S.Du J.Sun R.Li X.Yang D.Zhang S.Xiong C.Peng Y. React. Funct. Polym. 2003, 56: 17 - 18
Bertozzi CR.Bednarski MD. J. Org. Chem. 1991, 56: 4326 - 19
Cook RM.Adams JH.Hudson D. Tetrahedron Lett. 1994, 35: 6777 - 20
Schwabacher AW.Lane JW.Schiesher MW.Leigh KM.Johnson CW. J. Org. Chem. 1998, 63: 1727 - 21
Hervè G.Hahn DU.Hervè AC.Goodworth KJ.Hill AM.Hailes HC. Org. Biomol. Chem. 2003, 1: 427 - 22
Kohler N.Fryxell GE.Zhang M. J. Am. Chem. Soc. 2004, 126: 7206 - 23
Pilkington-Miska MA.Sarkar S.Writer MJ.Barker SE.Shamlou PA.Hart SL.Hailes HC.Tabor AB. Eur. J. Org. Chem. 2008, 2900 - 24
Svedhem S.Hollander CÅ.Shi J.Konradsson P.Liedberg B.Svensson S. J. Org. Chem. 2001, 66: 4494 - 25
Loiseau F.Hii KK.Hill AM. J. Org. Chem. 2004, 69: 639 - 26
Ehteshami GR.Sharma SD.Porath J.Guzman RZ. React. Funct. Polym. 1997, 35: 135 - 27
Voelcker NH.Klee D.Hanna M.Hoecker H.Bou JJ.de Ilarduya AM.Munoz-Guerra S. Macromol. Chem. Phys. 1999, 200: 1363 - 28
Drioli S.Benedetti F.Bonora GM. React. Funct. Polym. 2001, 48: 119 - 29
Ortega-Muñoz M.Lopez-Jaramillo J.Hernandez-Mateo F.Santoyo-Gonzales F. Adv. Synth. Catal. 2006, 348: 2410 - 30
Guo Z.Lei A.Liang X.Xu Q. Chem. Commun. 2006, 4512 - 31
Hancock WS.Battersby JE. Anal. Biochem. 1976, 71: 260 - 33
Ressler C.Banerjee N. J. Org. Chem. 1976, 41: 1336
References and Notes
The loading was calculated by treating 1 g of pegylated silica gel 3 with cleavage solution and weighting the recovered PEG.
34Analytical sample was treated with NaBH4 and analyzed with mass spectrometer. ESI-MS (most intense peaks): (n = 10) 541.4 [M + Na+]; (n = 11) 585.4 [M + Na+]; (n = 12) 629.9 [M + Na+].