Sigma-Aldrich Cysteamine 2-Chlorotrityl

Quality Level

200

Product Line

Novabiochem^®

Form

beads

Reaction Suitability

reaction type: Fmoc solid-phase peptide synthesis

Manufacturer/Tradename

Novabiochem^®

Application(S)

peptide synthesis

Functional Group

amine

Storage Temp.

2-8°C

Related Categories

Amino Acids, Resins & Reagents for Peptide Synthesis

General Description

An acid-labile resin for the preparation ofN-acyl orN-alkyl cysteamines. The free amino functionality of the resin-bound cysteamine can be readily acylated or reductively alkylated using standard procedures. Cleavage can be effected with electrophilic oxidants such as I₂or Tl(3) to produce a dimeric disulfide bridged product, or with 50-100% TFA to give the monomeric sulfhydryl product. Peptidylaminoethylthiols produced in this manner have been used to prepare PEG-conjugates by chemoselective ligation to pegylated maleimide . This method is particularly useful for forming intramolecular disulfide bridges in molecules containing two thiol groups where one is protected with Acm. For a similar application, see ^[2,3,4] .

Associated Protocols and Technical Articles
Cleavage and Deprotection Protocols for Fmoc SPPS

Literature references

J. Zhang, et Al. Poster 162 presented at the 16 American Peptide Symposium, Minneapolis, 1999.
A. v. Vliet, et Al. in ′Innovation & Perspectives in Solid Phase Synthesis, 2nd International Symposium′, R. Epton (Eds), Intercept UK Ltd., Andover, 1992, PP. 475.
A. v. Vliet, et Al. in ′Peptides 1992, Proc.22nd European Peptide Symposium′, C. H. Schneider & A. N. Eberle (Eds), ESCOM, Leiden, 1993, PP. 279.
A. v. Vliet, et Al. in ′Peptides, Chemistry, Structure, &Biology, Proc. 13th American Peptide Symposium′, R. S. Hodges & J. A. Smith (Eds), ESCOM, Leiden, 1994, PP. 151.

Linkage

Replaces: 01-64-0107

Analysis Note

Color (visual): white to yellow to beige
Appearance of substance (visual): beads
Loading (determined from the substitution of the Fmoc-Leu loaded resin): 1.00 - 2.00 mmol/g
Swelling Volume (in DMF): lot specific result
The polymer matrix is copoly (styrene-1% DVB), 200 - 400 mesh.Novabiochem is a registered trademark of Merck KGaA, Darmstadt, Germany