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Sigma-Aldrich

p-Nitrophenyl carbonate Merrifield resin

Novabiochem®

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Quality Level

product line

Novabiochem®

form

beads

reaction suitability

reaction type: Fmoc solid-phase peptide synthesis
reactivity: amine reactive

manufacturer/tradename

Novabiochem®

application(s)

peptide synthesis

storage temp.

15-25°C

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 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

Legal Information

Novabiochem is a registered trademark of Merck KGaA, Darmstadt, Germany

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable


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