Preparation of N-tBoc l-glutathione dimethyl and di-tert-butyl esters: Versatile synthetic building blocks

Bioorganic and Medicinal Chemistry

Volumn 15, Issue 2, 2007, Pages 1062-1066

  Falck, J R ^a   Sangras, Bhavani ^a   Capdevila, Jorge H ^b  

^a UNIVERSITY OF TEXAS SOUTHWESTERN MEDICAL CENTER   (United States)

^b VANDERBILT UNIVERSITY SCHOOL OF MEDICINE   (United States)

Author keywords

Amino acids and derivatives; Peptides; Protecting groups; Thioesters

Indexed keywords

2 PROPANOL; AMINE; CHLORIDE; DISULFIDE; GLUTATHIONE DERIVATIVE; GLUTATHIONE DISULFIDE; METHANOL; THIOESTER; TRIBUTYLPHOSPHINE; DRUG DERIVATIVE; DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS; ESTER; GLUTATHIONE; N TBOC L GLUTATHIONE DI TERT BUTYL ESTER; N TBOC L GLUTATHIONE DIMETHYL ESTER; N-TBOC L-GLUTATHIONE DI-TERT-BUTYL ESTER; N-TBOC L-GLUTATHIONE DIMETHYL ESTER; PALMITIC ACID; SOLVENT;

ARTICLE; CHROMATOGRAPHY; ESTERIFICATION; PALMITOYLATION; REACTION ANALYSIS; SAPONIFICATION; SYNTHESIS; CHEMISTRY; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; THIN LAYER CHROMATOGRAPHY;

CHROMATOGRAPHY, THIN LAYER; ESTERS; GLUTATHIONE; INDICATORS AND REAGENTS; MAGNETIC RESONANCE SPECTROSCOPY; MASS SPECTROMETRY; PALMITIC ACID; SOLVENTS;

EID: 33845308279     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2006.10.022     Document Type: Article

References (34)

1. Reid M., and Jahoor F.. Curr. Opin. Clin. Nutr. Metab. Care 3 (2000) 385-390
2. Masip L., Veeravalli K., and Georgiou G.. Antioxid. Redox Signal. 8 (2006) 753-762
3. Reid M., and Jahoor F. Curr. Opin. Clin. Nutr. Metab. Care 4 (2001) 65-71
4. Droge W., and Breitkreutz R. Proc. Nutr. Soc. 59 (2000) 595-600
5. Lorenson M.Y., and Jacobs L.S. Endocrinology 120 (1987) 365-372
6. Cnubben N.H.P., Rietjens I.M.C.M., Wortelboer H., van Zanden J., and van Bladeren P.J. Environ. Toxicol. Pharm. 10 (2001) 141-152
7. Shackelford R.E., Heinloth A.N., Heard S.C., and Paules R.S. Antioxid. Redox Signal. 7 (2005) 940-950
8. Vamvakas S., and Anders M.W. Adv. Exp. Med. Biol. 283 (1991) 13-24
9. Lauterburg B.H. Prog. Pharm. Clin. Pharm. 8 (1991) 201-213
10. Ingelman-Sundberg M. Chem. Biol. Interact. 133 (2001) 84-86
11. Review. Murphy R.C., and Zarini S. Prostaglandins Other Lipid Mediat. 68-69 (2002) 471-482
12. Spearman M.E., Prough R.A., Estabrook R.W., Falck J.R., Manna S., Leibman K.C., Murphy R.C., and Capdevila J. Arch. Biochem. Biophys. 242 (1985) 225-230
13. For a multi-step total synthesis of 3 from l-cysteine and an unsuccessful attempt directly from l-glutathione, see. Threadgill M.D., and Gledhill A.P. J. Org. Chem. 54 (1989) 2940-2949
14. Using l-glutathione see. Crich D., Krishnamurthy V., and Hutton T.K. J. Am. Chem. Soc. 128 (2006) 2544-2545
15. Su D., Ren X., You D., Li D., Mu Y., Yan G., Zhang Y., Luo Y., Xue Y., Shen J., Liu Z., and Luo G. Arch. Biochem. Biophys. 395 (2001) 177-184
16. Arisawa M., Ono T., and Yamaguchi M. Tetrahedron Lett. 46 (2005) 5669-5671
17. Kedrowski B.L., and Heathcock C.H. Heterocycles 58 (2002) 601-634
18. Anderson M.E., Powrie F., Puri R.N., and Meister A. Arch. Biochem. Biophys. 239 (1985) 538-548
19. Muraki M., and Mizoguchi T.. Chem. Pharm. Bull. 19 (1971) 1708-1713
20. Anderson G.W., and Callahan F.M. J. Am. Chem. Soc. 82 (1960) 3359-3363
21. Valerio R.M., Alewood P.F., and Johns R.B. Synthesis (1988) 786-789
22. Liu L., Tanke R.S., and Miller M.J. J. Org. Chem. 51 (1986) 5332-5337
23. Takeda K., Akiyama A., Nakamura H., Takizawa S., Mizuno Y., Takayanagi H., and Harigaya Y. Synthesis (1994) 1063-1066
24. Chevallet P., Garrouste P., Malawska B., and Martinez J. Tetrahedron Lett. 34 (1993) 7409-7412
25. Loffet A., Galeotti N., Jouin P., and Castro B. Tetrahedron Lett. 30 (1989) 6859-6860
26. Widmer U. Synthesis (1983) 135-136
27. Dhaon M.K., Olsen R.K., and Ramasamy K. J. Org. Chem. 47 (1982) 1962-1965
28. Ohta S., Shimabayashi A., Aona M., and Okamoto M. Synthesis (1982) 833-834
29. Shih I.-L., Chiu L.-C., Lai C.T., Liaw W.-C., and Tai D.-F. Biotechnol. Lett. 19 (1997) 857-859
30. Galzigna, L. PCT Int. Appl. (1992), WO 9200320 A1 19920109; CAN 116:152418; AN 1992:152418.
31. A similar strategy to improve the solubility of GSH by preparing a lipophilic S-derivative prior to esterification was published while this manuscript was in preparation see Ref. 12b.
32. A related procedure produced a mixture of 54% S-palmitoyl and 46% N-palmitoyl glutathione:. Vignais P.V., and Zabin I. Biochim. Biophys. Acta 29 (1958) 263-269
33. Zhu J., Hu X., Dizin E., and Pei D. J. Am. Chem. Soc. 125 (2003) 13379-13381
34. Zervas L., Photaki I., and Ghelis N. J. Am. Chem. Soc. 85 (1963) 1337-1341