Peptide synthesis based on t-Boc chemistry and solution photogenerated acids

Journal of Combinatorial Chemistry

Volumn 2, Issue 4, 2000, Pages 355-360

  Pellois, Jean Philippe ^a   Wang, Wei ^b   Gao, Xiaolian ^a  

^a University of Houston ^*  (United States)

^b UNIVERSITY OF TEXAS MEDICAL SCHOOL   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS; PEPTIDE; PLANT RESIN;

ARTICLE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; PHOTOCHEMISTRY; SOLUTION AND SOLUBILITY; SYNTHESIS;

CHROMATOGRAPHY, HIGH PRESSURE LIQUID; INDICATORS AND REAGENTS; PEPTIDES; PHOTOCHEMISTRY; RESINS, PLANT; SOLUTIONS;

EID: 0034222875     PISSN: 15204766     EISSN: None     Source Type: Journal    
DOI: 10.1021/cc0000139     Document Type: Article

References (24)

1. (a) Merrifield, R. B. J. Am. Chem. Soc. 1963, 85, 2149-2154.
2. (b) Merrifield, R. B. Science 1986, 232, 341-347.
3. (a) Lam, K. S.; Salmon, S. E.; Hersh, E. M.; Hruby, V. J.; Kazmierski, W. M.; Knapp, R. J. Nature 1991, 354, 82-84.
4. (b) Houghten, R. A.; Pinilla, C.; Blondelle, S. E.; Appel, J. R.; Dooley, C. T.; Cuervo, J. H. Nature 1991, 354, 84-86.
5. (c) Combinatorial peptide and nonpeptide libraries. A handbook; Jung, G., Ed.; VCH: New York, 1996; and reference cited therein,
6. (d) Solid-phase peptide synthesis; Fields, G., Ed.; Methods in Enzymology, Vol. 289; Academic Press: New York, 1997; and reference cited therein,
7. (e) Fodor, S. P. A.; Leighton, J.; Pirrung, M. C.; Stryer, L.; Lu, A. T.; Solas, D. Science 1991, 251, 767-773.
8. (f) Cho, C. Y.; Morgan, E. J.; Cherry, S. R.; Stephans, J. C.; Fodor, S. P. A.; Adams, C. L.; Sundaram, A.; Jacobs, J. W.; Schultz, P. G. Science 1993, 267, 1303-1305.
9. (a) Rodda, S.; Tribbick, G.; Geysen, M. Epitope mapping. In Combinatorial peptide and nonpeptide libraries. A handbook; Jung, G.; Ed.; VCH: New York, 1996; pp 303-326.
10. (b) Udaka, K.; Wiesmuller, K.-H.; Kienle, S.; Feiertag, S.; Jung, G.; Waiden, P. Random peptide libraries as tools in basic and applied immunology. In Combinatorial peptide and nonpeptide libraries. A handbook; Jung, G., Ed.; VCH: New York, 1996; pp 349-362.
11. Furka, A. Chemical synthesis of peptide libraries. In Combinatorial peptide and nonpeptide libraries. A handbook; Jung, G., Ed.; VCH: New York, 1996; pp 111-138.
12. (a) Gao, X.; Yu, P.; Leproust, E.; Sonigo, L.; Pellois, J. P.; Zhang, H. J. Am. Chem. Soc. 1998, 720, 12698-12699.
13. (b) Leproust, E.; Pellois, J. P.; Yu, P.; Zhang, H.; Srivannavit, O.; Gulari, E.; Zhou, X.; Gao, X. J. Comb. Chem. 2000, 2, 349-354.
14. Stewart, J. M.; Young, J. D. Solid phase peptide synthesis, 2nd ed.; Pierce Chemical Co.: Rockford, IL, 1984.
15. Pintchovski, F.; Price, J. B.; Tobin, P. J.; Peavy, J.; Kobold, K. J. Electrochem. Soc. 1979, 126, 1428-1431.
16. (a) Balachander, N.; Sukenik, C. N. Langmuir 1990, 6, 1621-1627.
17. (b) Heise, A.; Menzel, H.; Yim, H.; Foster, M. D.; Wieringa, R. H.; Scheuten, A. J.; Erb. V.; Stamm, M. Langmuir 1997, 13, 723-728.
18. (a) MacDonald, S. A.; Willson, C. G.; Fréchet, J. M. Acc. Chem. Res. 1994, 27, 151-157.
19. (b) Willson, C. G. Introduction to microlithography. Thompson, L. F., Willson, C. G., Bowden, M. J., Eds.; In ACS Professional Reference Book, 2nd ed.; American Chemical Society: Washington, DC, 1994; pp 138-267.
20. (c) PGA reagents are commonly used in solid-phase reactions for deprotection of the t-Boc group on polymer chains (e.g., poly-tert-butyloxy-carbonyloxystyrene)), which is a key step in photoresist microfabrication processes. The removal of the Boc group exposes polar groups, such as hydroxyl groups on the phenyl moiety of the polystyrene. The resultant deprotected polymer becomes more soluble in basic solutions and is stripped away to produce microfeatures on surfaces of microelectronic devices, such as computer chips.
21. DeVoe, R. J.; Olofson, P. M.; Sahyun, M. R. V. Adv. Photochem. 1992, 17, 314-355.
22. (a) Beecher, J. E.; McGall, G. H.; Goldberg, M. Polym. Mater. Sci. Eng. 1997, 76, 394-395.
23. (b) Beecher, J. E.; McGall, G. H.; and Goldberg, M. Polym. Mater. Sci. Eng. 1997, 76, 597-598.
24. (c) Wallraff, G.; Labadie, J.; Brock, P.; DiPietro, R.; Nguyen, T.; Huynh, T.; Hinsberg, W.; MaGall, G. Chemtech. 1997, 27, 22-32.