New methods for side-chain protection of cysteine

Organic Letters

Volumn 3, Issue 8, 2001, Pages 1205-1208

  West, Christopher W ^a   Estiarte, M Angels ^a   Rich, Daniel H ^a  

^a UNIVERSITY OF WISCONSIN MADISON   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CYSTEINE; PEPTIDE; THIOL DERIVATIVE;

ARTICLE; CHEMICAL MODEL; CHEMISTRY; METHODOLOGY; ORGANIC CHEMISTRY;

CHEMISTRY, ORGANIC; CYSTEINE; MODELS, CHEMICAL; PEPTIDES; SULFHYDRYL COMPOUNDS;

EID: 0035912338     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol015678d     Document Type: Article

References (24)

1. Carpino, L. A.; Han, G. Y. J. Am. Chem. Soc. 1970, 92, 5748.
2. Nicolaou, K. C.; Winssinger, N.; Pastor, J.; DeRoose, F. J. Am. Chem. Soc. 1997, 119, 449.
3. (a) Sund, C.; Agback, P.; Koole, L. H.; Sandstroem, A.; Chattopadhyaya, J. Tetrahedron 1992, 48, 695.
4. (b) Lin, J.; Shaw, B. R. J. Chem. Soc., Chem. Commun. 1999, 1517.
5. Gioeli, C.; Chattopadhyaya, J. B. J. Chem. Soc., Chem. Commun. 1982, 672.
6. (a) Ruiz-Gayo, M.; Albericio, F.; Pedroso, E.; Giralt, E. J. Chem. Soc., Chem. Commun. 1986, 1501.
7. (b) Corey, E. J.; Gin, D. Y.; Kania, R. S. J. Am. Chem. Soc. 1996, 118, 9202.
8. (c) Ponsali, B.; Giralt, E.; Andreu, D. Tetrahedron 1990, 46, 8255.
9. (a) Bodanszky, M.; Bednarek, M. A. Int. J. Peptide Protein Res. 1982, 20, 434.
10. (b) Albericio, F.; Nicolas, E.; Rizo, J.; Ruiz-Gayo, M.; Pedroso, E.; Giralt, E. Synthesis 1990, 119.
11. Threadgill, M. D.; Gledhill, A. P. J. Org. Chem. 1989, 54, 2940.
12. 1H NMR after a reaction time of 4 h.
13. At higher concentrations of reactants and temperatures above 40 °C during workup, the deprotection of the S-Fmoc group is faster.
14. Addition of nucleophiles to dibenzofulvene: Carpino, L. A.; Han, G. Y. J. Org. Chem. 1972, 37, 3404.
15. In an additional experiment compound 3 was treated with a 1:1 mixture of DIEA:HOSu, yielding a mixture of starting material and disulfide in a 1:1 ratio.
16. Schnabel, E.; Stoltefuss, J.; Offe, H. A.; Klaude, E. Justus Liebigs Ann. Chem. 1971, 743, 57.
17. The S-Fmoc group in amide derivative 8 is more stable under basic conditions than esters 2 or 5.
18. Zhang, H. X.; Guibe, F.; Balavoine, G. Tetrahedron Lett. 1988, 29, 623.
19. Krapcho, A. P.; Kuell, C. S. Synth. Comm. 1990, 20(16), 2559.
20. (a) Meng, Q.; Thibblin, A. J. Am. Chem. Soc. 1997, 119, 4834.
21. (b) O'Ferrall, R. A. M.; Larkin, F.; Walsh, P. J. Chem. Soc., Perkin Trans. 2 1982, 1573.
22. Bodanszky, M.; Deshmane, S. S.; Martinez, J. J. Org. Chem. 1979, 44, 1622.
23. Vedejs, E.; Klapars, A.; Naidu, B. N.; Piotrowski, D. W.; Tucci, F. C. J. Am. Chem. Soc. 2000, 122, 5401.
24. Alternatively, the reaction might proceed via an imide anion formed six atoms away from the Fmoc proton.