8.55029
N-Cyclohexylcarbodiimide,N′-methyl polystyrene
Novabiochem®
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About This Item
UNSPSC Code:
13111023
NACRES:
NA.22
Quality Level
product line
Novabiochem®
form
beads
reaction suitability
reaction type: solution phase peptide synthesis
reactivity: carboxyl reactive
manufacturer/tradename
Novabiochem®
application(s)
peptide synthesis
storage temp.
2-8°C
General description
N-Cyclohexylcarbodiimide, N-methyl polystyrene [1] is an ideal tool for mediating solution phase coupling reactions. Typically, the amine and carboxylic acid are treated with a 2-3 fold excess of resin in DCM or DMF [2,3]; a slight excess of carboxyl component over amine component is often used to help drive the reaction to completion. As excess acid and urea by-products remain attached to the resin at the end of the reaction, the product can normally be isolated pure by filtration and evaporation of the reaction mixture. Reactions can be accelerated by the addition of auxiliary nucleophiles such as HOBt; these can be removed using polyamine- or TBD-polystyrene. This resin has also been used in conjunction with DMAP to mediate ester formation [4].
Associated Protocols and Technical Articles
Protocols for Loading of Peptide Synthesis Resins
Literature references
[1] G.M Weinshenker, et al. (1988) Org. Synth., Coll. Vol. VI, 951.
[2] Y. Guan, et al. (2000) J. Comb. Chem., 2, 297.
[3] K. Senton, et al. (2003) J. Comb. Chem., 5, 336.
[4] M. Cano, et al. (2002) J. Org. Chem., 67, 129.
Associated Protocols and Technical Articles
Protocols for Loading of Peptide Synthesis Resins
Literature references
[1] G.M Weinshenker, et al. (1988) Org. Synth., Coll. Vol. VI, 951.
[2] Y. Guan, et al. (2000) J. Comb. Chem., 2, 297.
[3] K. Senton, et al. (2003) J. Comb. Chem., 5, 336.
[4] M. Cano, et al. (2002) J. Org. Chem., 67, 129.
Linkage
Replaces: 01-64-0211
Analysis Note
Color (visual): slightly beige to brown
Appearance of substance (visual): beads
Loading (determined by HPLC after reaction of Z-Phe-OH with cyclohexylamine): ≥ 1.3 mmol/g
Swelling Volume (in CH₂Cl₂): lot specific result
The polymer matrix is copoly (styrene-2 % DVB), 200 - 400 mesh.
Appearance of substance (visual): beads
Loading (determined by HPLC after reaction of Z-Phe-OH with cyclohexylamine): ≥ 1.3 mmol/g
Swelling Volume (in CH₂Cl₂): lot specific result
The polymer matrix is copoly (styrene-2 % DVB), 200 - 400 mesh.
Legal Information
Novabiochem is a registered trademark of Merck KGaA, Darmstadt, Germany
Storage Class Code
11 - Combustible Solids
WGK
WGK 1
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Certificates of Analysis (COA)
Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.
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