p-Nitrophenyl carbonate Merrifield resin

Description

• General description: Resin-bound p-nitrophenyl carbonate esters react readily with amines to provide the corresponding resin-bound carbamate. Leznoff [1] was the first to demonstrate the utility of such resins in solid phase synthesis with the preparation of mono-acylated diamines from symmetrical diamines. Dress man, et al. [2] have used carbamate linked resin-bound amino acid amides to make hydantoins via a base-mediated cyclization/ cleavage strategy; a similar approach has also been used to prepare quinazolidine-2,4-diones [3]. Gordon, et al. [4] have used p-nitrophenyl carbonate Merrifield resin to immobilize a ketone linker through a phenyl carbonate linkage. Loading of this resin can be quantified by measuring the release of p-nitrophenolate [5].Associated Protocols and Technical Articles Protocols for Loading of Peptide Synthesis Resins Literature references [1] D. M. Dixit, et al. (1978) Israel J. Chem., 17, 248. [2] B. A. Dressman, et al. (1996) Tetrahedron Lett., 37, 937. [3] L. Gouilleux, et al. (1996) Tetrahedron Lett., 37, 7031.[4] K. Gordon, et al. (2000) Tetrahedron Lett., 41, 8621. [5] A. Paio, et al. (2003) Tetrahedron Lett.,44, 1867.
• Linkage: Replaces: 01-64-0131
• Analysis Note: Color (visual): white to yellow to beigeAppearance of substance (visual): beadsLoading (photometric determination of p-nitrophenyl released upon treatment with piperidin): 0.80 - 1.40 mmol/gSwelling Volume (in DMF): lot specific resultThe polymer matrix is copoly ( styrene - 1% DVB ), 100 - 200 mesh
• Legal Information: Novabiochem is a registered trademark of Merck KGaA, Darmstadt, Germany