An acid-labile resin for the preparation of N-acyl or N-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 I2 or 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 [1]. 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
[1] J. Zhang, et al. Poster 162 presented at the 16 American Peptide Symposium, Minneapolis, 1999.
[2] 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.
[3] 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.
[4] 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.
Legal Information
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