Sigma-Aldrich 2-Chlorotrityl Chloride Re

Quality Level

200

Product Line

Novabiochem^®

Form

beads

Reaction Suitability

reaction type: Fmoc solid-phase peptide synthesis

Manufacturer/Tradename

Novabiochem^®

Application(S)

peptide synthesis

Storage Temp.

2-30°C

Related Categories

Amino Acids, Resins & Reagents for Peptide Synthesis

General Description

2-Chlorotrityl chloride resin is an extremely versatile, acid-labile resin for the solid phase immobilization of carboxylic acids ^{[1,2,3,4,5,6, 20]} , alcohols ^{[7,8,9, 20]} , phenols ^{[10,11,12,13, 20]} and amines ^{[14,15,16,17,18,19,20]} , imidazoles ^[20] and hydroxylamines ^[21,22] . Release of these functionalities is generally achieved using 1-50% TFA in DCM containing 5% TIS, although carboxylic acids can also be cleaved from this support with AcOH/TFE/DCM ^{[1,2,3,4,5,6]} ,0.5% TFA in DCM, or HFIP in DCM ^[23] _.

Associated Protocols and Technical Articles
Protocols for Loading of Peptide Synthesis ResinsLiterature references

K. Barlos, et Al. (1989)Tetrahedron Lett.,30, 3947.
K. Barlos, et Al. (1989)Tetrahedron Lett.,30, 3943.
K. Barlos, et Al. (1991)Angew. Chem. Int. Ed. Engl.,30, 590.
K. Barlos, et Al. (1991)Int. J. Peptide Protein Res.,37, 513.
^[5] K. Barlos, et Al. (1991) Int. J. Peptide Protein Res.,38, 562.
^[6] K. Barlos, et Al. (1991)Int. J. Peptide Protein Res.,38, 555.
^{[ 7]} H. Wenschuh, et Al. in ′Peptides 1994, Proc. 23rd European Peptide Symposium′, H. Maia (Eds), ESCOM, Leiden, 1995, PP. 287.
^[8] H. Wenschuh, et Al. (1995)J. Org. Chem.,60, 405.
^[9] B. B. Shankar, et Al. (1998)Tetrahedron Lett.,39, 2447.
^[10] Z. Zhu & B. Mckittrick (1998)Tetrahedron Lett.,39, 7479.
^[11] U. Heinelt, et Al. (2001)Bioorg. Med. Chem. Lett.,11, 227.
^[12] K. J. Elgie, et Al. (2000)Tetrahedron Lett.,41, 2753.
^[13] S. Batra, et Al. (2000)Tetrahedron Lett.,41, 5971.
^[14] M. Cardno, et Al. (1995)J. Chem. Soc., Chem. Commun., 2163.
^[15] I. A. Nash, et Al. (1996)Tetrahedron Lett.,37, 2625.
^[16] W. J. Hoekstra, et Al. (1997)Tetrahedron Lett.,38, 2629.
^[17] J. Perumattan, et Al. (1998)Mol. Div.,3, 121.
^[18] J. J. McNally, et Al. (1998)Tetrahedron Lett.,39,967.
^[19] M. A. Youngman & S. L. Dax (1997)Tetrahedron Lett.,38, 6347.
^[20] A. Bernhardt, et Al. (1997)J. Peptide Res.,50, 143.
^[21] S. L. Mellor, et Al. (1997)Tetrahedron Lett.,38, 3311.
^[22] M. M. Meloni & M. Taddei (2001)Org. Lett.,3, 337.
^[23] R. Bollhagen, et Al. (1994)J. Chem. Soc ., Chem. Commun., 2559.

Application

• Efficient Synthesis of Protein Mimics by Sequential Native Chemical Ligation:This study utilized 2-Chlorotrityl chloride resin (100-200 mesh, 1% DVB) for solid-phase peptide synthesis, highlighting its effective use in complex peptide assembly processes. (Kruijtzer & Liskamp).

Linkage

Replaces: 01-64-0114

Analysis Note

Colour (visual): white to yellow to beige
Appearance of substance (visual): beads
Loading (determined from the substitution of the Fmoc-Ala-Leu loaded resin): 1.00 - 1.80 mmol/g
Swelling Volume (in CH₂Cl₂): 2.0 - 5.0 mL/g
Total swelling volume acc. Houben Weyl (in CH₂Cl₂): ≥ 4.2 mL/g
The polymer matrix is copoly (styrene-1 % DVB) 100 - 200 mesh.Novabiochem is a registered trademark of Merck KGaA, Darmstadt, Germany