p-Nitrophenyl carbonate Merrifield resin

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.

Color (visual): white to yellow to beige
Appearance of substance (visual): beads
Loading (photometric determination of p-nitrophenyl released upon treatment with piperidin): 0.80 - 1.40 mmol/g
Swelling Volume (in DMF): lot specific result
The polymer matrix is copoly ( styrene - 1% DVB ), 100 - 200 mesh

Replaces: 01-64-0131

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