A peptide coupling reagent. Widely applied in combination with triphenylphosphine,1 in macrolactonization via high-dilution cyclization of the 2-pyridine thioester,2 and for the activation of glycosides by combining with tri-n-butylphosphine.3 Also used in the reactions of histamine, the natural dipeptide carcinine (β-Ala-HA), and its analogs with 5'-monodeoxyribonucleotides (dNMP),4 preparation of boc-cys(S-Pyr)-OH and Z-Cys(S-Pyr)-OH (Pyr = 2-pyridyl) by addition of their cysteine derives,5 and synthesis of 3-(2-pyridyldithio)propionic acid.6 An organosulfur ligand used for synthesis of novel coordination polymers,7,8 and for making new metal complexs.9,10 A reagent for thiol-disulfide exchange reaction useful in spectrophotometric detection, HPLC-UV, and micellar electrokinetic chromatography.11,12
Reference
1. J. Am. Chem. Soc. 1968, 90, 4490.
2. J. Am. Chem. Soc. 1975, 97, 653.
3. Tetrahedron 1991, 47, 6435.
4. Russ. Chem. Bull. 2002, 51, 1940.
5. J. Peptide Res. 1998, 51, 290.
6. Synth. Comm. 1998, 28, 3213.
7. Eur. J. Inorg. Chem. 2006, 2746.
8. Inorg. Chem. 2008, 47, 9128.
9. Eur. J. Inorg. Chem. 2008, 3123.
10. Z. Naturforsch. B 2005, 60, 373.
11. Anal. Chim. Acta 2005, 533, 179
12. J. Chromatogr. A 2003, 990, 197.