Convenient supported recyclable material based on dihydrolipoyl-residue for the reduction of disulfide derivatives

Tetrahedron Letters

Volumn 51, Issue 25, 2010, Pages 3309-3311

  Bienvenu, Céline ^a   Greiner, Jacques ^a   Vierling, Pierre ^a   Giorgio, Christophe Di ^a  

^a UNIVERSITÉ CÔTE D'AZUR   (France)

Author keywords

Dihydrolipoic acid; Disulfide; Polymer supported reducing agent

Indexed keywords

DIHYDROLIPOAMIDE ACETYLTRANSFERASE; DISULFIDE; POLYMER; REDUCING AGENT; RESIN; THIOCTIC ACID; THIOL DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; ONE POT SYNTHESIS; RECYCLING; REDUCTION; SOLID;

EID: 77953229798     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2010.04.079     Document Type: Article

References (24)

1. Jocelyn P.C., and Biochemistry of the SH Group. The Occurrence, Chemical Properties, Metabolism, and Biological Function of Thiols and Disulfides (1972), Academic Press, London
2. Oae S. Organic Sulfur Chemistry: Structure and Mechanism (1991), CRC Press, Boca Raton, FL
3. Patai, S. The Chemistry of the Thiol Group; S. Patai, Ed.; J. Wiley and Sons Ltd: London, 1974.
4. Love J.C., Estroff L.A., Kriebel J.K., Nuzzo G.R., and Whitesides G.M. Chem. Rev. 105 (2005) 1103-1170
5. Saito G., Swanson J.A., and Lee K.D. Adv. Drug Deliv. Rev. 55 (2003) 199-215
6. Zuber G., Dauty E., Nothisen M., Belguise P., and Behr J.-P. Adv. Drug Deliv. Rev. 52 (2001) 245-253
7. Balakirev M., Schoehn G., and Chroboczek J. Chem. Biol. 7 (2000) 813-819
8. Le Gourrierec L., Di Giorgio C., Greiner J., and Vierling P. Tetrahedron 64 (2008) 2233-2240
9. Le Gourrierec L., Di Giorgio C., Greiner J., and Vierling P. New J. Chem. 32 (2008) 2027-2042
10. Parker A.J., and Kharasch N. Chem. Rev. 59 (1959) 583-628
11. Cleland W.W. Biochemistry 3 (1964) 480-482
12. Gorecki M., and Patchornik A. Biochim. Biophys. Acta, Protein Struct. 303 (1973) 36-43
13. Gorecki, M.; Patchornik, A. US Patent 3,914,205, 1975.
14. Fujimoto A., Endo T., and Okawara M. Makromol. Chem. 175 (1974) 3597-3602
15. Sperling R., and Gorecki M. Biochemistry 13 (1974) 2347-2353
16. Amos R.A., and Fawcett S.M. J. Org. Chem. 49 (1984) 2637-2639
17. Tamami B., and Goudarzian N. J. Chem. Soc., Chem. Commun. (1994) 1079
18. Linetsky M., LeGrand R.D., Mossine V.V., and Ortwerth B.J. Appl. Biochem. Biotechnol. 94 (2001) 71-96
19. Garcia-Martin F., Quintanar-Audelo M., Garcia-Ramos Y., Cruz L.J., Gravel C., Furic R., Cote S., Tulla-Puche J., and Albericio F. J. Comb. Chem. 8 (2006) 213-220
20. 4 (5 equiv, 1.85 mmol) aqueous solution (deionized and degazed water) for 30 min. The resulting slurry was rinsed with water (twice) and then acidified with 0.1 M acetic acid (twice) and rinsed again with water.
21. Kaiser E., Colescott R.L., Bossinger C.D., and Cook P.I. Anal. Biochem. 34 (1970) 595-598
22. Ellman G.L. Arch. Biochem. Biophys. 82 (1959) 70-77
23. 19
24. 2 (10 mg, 0.0025 mmol) and diethylamine (3 μL, 0.0065 mM) in DMF (5 mL), and the mixture was stirred for 1 h at room temperature. The resin was filtered off and washed with DMF (2 × 5 mL). The MeOPEG-SH was recovered by evaporation under reduced pressure (98.7% of sulfhydryl content).