Novel S-Xanthenyl Protecting Groups for Cysteine and Their Applications for the Nα-9-Fluorenylmethyloxycarbonyl (Fmoc) Strategy of Peptide Synthesis

Journal of Organic Chemistry

Volumn 62, Issue 12, 1997, Pages 3841-3848

  Han, Yongxin ^a   Barany, George ^a  

^a UNIVERSITY OF MINNESOTA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001525365     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo961882g     Document Type: Article

References (34)

1. A preliminary account of this work was reported at the 14th American Peptide Symposium, Columbus, OH, June 18-23, 1995. Solé, N. A.; Han, Y.; Vágner, J.; Gross, C. M.; Tejbrant, J.; Barany, G. In Peptides-Chemistry, Structure and Biology: Proceedings of the Fourteenth American Peptide Symposium; Kaumaya, P. T. P., Hodges, R. S., Eds.; ESCOM Science Publishers: Leiden, The Netherlands, 1996; pp 113-114.
2. Taken in part from the Ph.D. thesis of Y. Han, University of Minnesota, October, 1996.
3. 3, thallium(III) tris(trifluoroacetate); Trt (or trityl), triphenylmethyl; Xan, 9H-xanthen-9-yl. Amino acid symbols denote the L-configuration unless indicated otherwise.
4. Reviews: (a) Barany, G.; Merrifield, R. B. In The Peptides, Analysis, Synthesis, Biology; Gross, E., Meienhofer, J., Eds.; Academic Press: New York, 1979; Vol. 2, pp 1-284. (b) Andreu, D.; Albericio, F.; Solé, N. A.; Munson, M. C.; Ferrer, M.; Barany, G. In Methods in Molecular Biology; Pennington, M. W., Dunn, B. M., Eds.; Humana Press: Totowa, NJ, 1994; Vol. 35; pp 91-169. (c) Moroder, L.; Besse, D.; Musiol, H.-J.; Rudolph-Böhner, S.; Siedler, F. Biopolymers (Peptide Science) 1996, 50, 207-234.
5. Reviews: (a) Barany, G.; Merrifield, R. B. In The Peptides, Analysis, Synthesis, Biology; Gross, E., Meienhofer, J., Eds.; Academic Press: New York, 1979; Vol. 2, pp 1-284. (b) Andreu, D.; Albericio, F.; Solé, N. A.; Munson, M. C.; Ferrer, M.; Barany, G. In Methods in Molecular Biology; Pennington, M. W., Dunn, B. M., Eds.; Humana Press: Totowa, NJ, 1994; Vol. 35; pp 91-169. (c) Moroder, L.; Besse, D.; Musiol, H.-J.; Rudolph-Böhner, S.; Siedler, F. Biopolymers (Peptide Science) 1996, 50, 207-234.
6. Reviews: (a) Barany, G.; Merrifield, R. B. In The Peptides, Analysis, Synthesis, Biology; Gross, E., Meienhofer, J., Eds.; Academic Press: New York, 1979; Vol. 2, pp 1-284. (b) Andreu, D.; Albericio, F.; Solé, N. A.; Munson, M. C.; Ferrer, M.; Barany, G. In Methods in Molecular Biology; Pennington, M. W., Dunn, B. M., Eds.; Humana Press: Totowa, NJ, 1994; Vol. 35; pp 91-169. (c) Moroder, L.; Besse, D.; Musiol, H.-J.; Rudolph-Böhner, S.; Siedler, F. Biopolymers (Peptide Science) 1996, 50, 207-234.
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9. Reviews: (b) Atherton, E.; Sheppard, R. Solid Phase Peptide Synthesis: A Practical Approach; IRL Press: Oxford, 1989. (c) Fields, G. B.; Tian, Z.; Barany, G. In Synthetic Peptides: A User's Guide; Grant, G., Ed.; W. H. Freeman and Co.: Salt Lake City, UT, 1992; pp 77-183.
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18. ω-amide function of asparagine and glutamine. See: Han, Y.; Solé, N. A.; Tejbrant, J.; Barany, G. Pept. Res. 1996, 9, 166-173.
19. Independent of our studies, Voelter has reported that the 9-phenylxanthen-9-yl (pixyl) group, used widely in O-protection in nucleoside chemistry, can be used for thiol protection. See: Echner, H; Voelter, W. In Innovation and Perspectives in Solid Phase Synthesis: Peptides, Polypeptides and Oligonucleotides; Epton, R., Ed.; Intercept Ltd.: Andover, England, 1992; pp 371-375.
20. Han, Y.; Bontems. S. L.; Hegyes, P.; Munson, M. C.; Minor, C. A.; Kates, S. A.; Albericio, F.; Barany, G. J. Org. Chem. 1996, 61, 6326-6339, and references cited therein.
21. 3) δ 7.23 (d, J = 7.0 Hz, 1H), 7.19 (d, J = 7.5 Hz. 1H), 6.98-7.05 (m, 3H), 6.81 (d, J = 2.5 Hz. 1H), 6.78 (dd, J = 2.5 and 8.5 Hz, 1H), 4.63 (s, 2H), 3.78 (s, 3H).
22. Munson, M. C.; Barany, G. J. Am. Chem Soc. 1993, 115, 10203-10216, and references cited therein.
23. Albericio, F.; Kneib-Cordonier, N.; Biancalana, S.; Gera, L.; Masada L. I.; Hudson, D.; Barany, G. J. Org. Chem. 1990, 55, 3730-3743.
24. (a) Barany, G.; Albericio, F.; Solé, N. A.; Griffin, G. W.; Kates, S. A.; Hudson, D. In Peptides 1992: Proceedings of the Twenty-Second European Peptide Symposium; Schneider, C. H.; Eberle, A. N., Eds.; ESCOM Science Publishers: Leiden, The Netherlands, 1993; pp 267-268.
25. (b) Zalipsky, S.; Chang, J. L.; Albericio, F.; Barany, G. React. Polym. 1994, 22, 243-258, and references cited therein.
26. The use of a combination of anisole with β-mercaptoethanol to scavenge acidolytic cleavage/deprotection reactions was first proposed by: (a) Grandas, A.; Pedroso, E.; Giralt, E.; Van Rietschoten J. Tetrahedron 1986, 42, 6703-6711;
27. see also: (b) Kneib-Cordonier, N.; Albericio, P.; Barany, G. Int. J. Pept. Protein Res. 1990, 35, 527-538.
28. (a) García-Echeverría, C.; Albericio, F.; Pons, M.; Barany, G.; Giralt, E. Tetrahedron Lett. 1989, 30, 2441-2444.
29. (b) Albericio, F.; Hammer, R. P.; García-Echeverría, C.; Molins, M. A.; Chang, J. L.; Munson, M. C.; Pons, M.; Giralt, E.; Barany, G. Int. J. Pept. Protein Res. 1991, 33, 402-413.
30. Yajima, H.; Fujii, N.; Funakoshi, S.; Watanabe, T.; Murayama, E.; Otaka, A. Tetrahedron 1988, 44, 805-819.
31. The occurrence of racemization, and conditions for minimization of this serious problem, are the subject of a separate report: Han, Y.; Albericio, F.; Barany, G. J. Org. Chem. 1997, 62, in press.
32. (a) Barany, G.; Chen, L.; Annis, I. ABRF '96: Biomolecular Techniques, An International Symposium Sponsored by The Association of Biomolecular Resource Facilities, San Francisco, CA, March 30-April 2, 1996.
33. (b) Barany, G.; Chen, L. In Innovation and Perspectives in Solid Phase Synthesis & Combinatorial Chemical Libraries: Biomedical & Biological Applications, 1996; Epton, R., Ed.; Mayflower Scientific Ltd.: Kingswinford, England, 1996; pp 181-186.
34. Two aromatic protons were resolved because the title Cys derivative exists as a diastereomeric mixture.