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Titolo:
Polytetrahydrofuran cross-linked polystyrene resins for solid-phase organic synthesis
Autore:
Toy, PH; Reger, TS; Garibay, P; Garno, JC; Malikayil, JA; Liu, GY; Janda, KD;
Indirizzi:
Scripps Clin & Res Inst, Dept Chem, La Jolla, CA 92037 USA Scripps Clin & Res Inst La Jolla CA USA 92037 hem, La Jolla, CA 92037 USA Scripps Clin & Res Inst, Skaggs Inst Chem Biol, La Jolla, CA 92037 USA Scripps Clin & Res Inst La Jolla CA USA 92037 iol, La Jolla, CA 92037 USA Wayne State Univ, Dept Chem, Detroit, MI 48202 USA Wayne State Univ Detroit MI USA 48202 v, Dept Chem, Detroit, MI 48202 USA Aventis Pharmaceut Inc, Bridgewater, NJ 08807 USA Aventis Pharmaceut Inc Bridgewater NJ USA 08807 Bridgewater, NJ 08807 USA
Titolo Testata:
JOURNAL OF COMBINATORIAL CHEMISTRY
fascicolo: 1, volume: 3, anno: 2001,
pagine: 117 - 124
SICI:
1520-4766(200101/02)3:1<117:PCPRFS>2.0.ZU;2-C
Fonte:
ISI
Lingua:
ENG
Soggetto:
PEPTIDE-SYNTHESIS; POLYMER SUPPORTS; COMBINATORIAL CHEMISTRY; REAGENTS; STYRENE; BEADS; PURIFICATION; AMINOMETHYL; STRATEGIES; CATALYSTS;
Tipo documento:
Article
Natura:
Periodico
Settore Disciplinare:
Life Sciences
Physical, Chemical & Earth Sciences
Citazioni:
68
Recensione:
Indirizzi per estratti:
Indirizzo: Janda, KD Scripps Clin & Res Inst, Dept Chem, 10550 N Torrey Pines Rd, La Jolla, CA 92037 USA Scripps Clin & Res Inst 10550 N Torrey Pines Rd La Jolla CA USA 92037
Citazione:
P.H. Toy et al., "Polytetrahydrofuran cross-linked polystyrene resins for solid-phase organic synthesis", J COMB CHEM, 3(1), 2001, pp. 117-124

Abstract

Currently, divinylbenzene cross-linked polystyrene (DVB-PS) is the polymerof choice for use in solid-phase organic synthesis (SPOS). While much research has been directed toward the optimization of linker groups for the attachment of compounds to the polymer, the development of new polymers themselves has been relatively neglected. In an attempt to overcome the shortcomings of DVB-PS and to develop new polymers with optimum properties for use in organic synthesis, we have prepared a series of polystyrene polymers thatincorporate flexible polytetrahydrofuran (PTHF) based cross-linkers. The objective of incorporating PTHF into the polymers was to slightly increase the overall polarity of the polymer and thus render the resins more organic solvent-like. Since the degree to which a resin swells in and absorbs a particular solvent correlates to how well substrates attached to the polymer are solvated, we compared the swelling of our new resins to commercially available DVB-PS resins, In all cases, we found that our resins swelled to a much greater extent than do DVB-PS resins, and their use should therefore allow for SPOS reaction conditions that more closely mimic homogeneous solution-phase conditions. It was also found that the PTHF chain length of the cross-linker does not affect the level of swelling since all of our cross-linkers afford resins with comparable levels of increased swelling. Furthermore, we have examined the utility of our resins in directed ortho-metalation reactions and found that the increased swelling of our resins allows for isolation of reaction products in yields comparable to what is achieved usingstandard solution-phase conditions.

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Documento generato il 11/07/20 alle ore 19:47:25