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Polypeptide Formation by Heating N-t-Butyloxycarbonyl Acidic Amino Acid Derivatives
Corresponding Author(s) : T. Munegumi
Asian Journal of Chemistry,
Vol. 26 No. 15 (2014): Vol 26 Issue 15
Abstract
An acid labile N-protecting group for amino acids, t-butyloxycarbonyl (Boc) group has deprotected at elevated temperatures. The study describes an application of the lability on heating to synthesis of polypeptides from acidic amino acids. t-Butyloxycarbonyl-acidic amino acids (aspartic acid, glutamic acid and b-aminoglutaric acid) and their anhydrides were heated at the higher temperatures than their melting points. Anhydrides of t-butyloxycarbonyl-aspartic acid and t-butyloxycarbonyl-b-aminoglutaric acid gave polypeptides. Thermal analyses of the substrates clarified the pathway of the polypeptide formation.
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- S.W. Fox, J.E. Johnson and M. Middlebrook, J. Am. Chem. Soc., 77, 1048 (1955); doi:10.1021/ja01609a081.
- K. Harada, J. Org. Chem., 24, 1662 (1959); doi:10.1021/jo01093a009.
- S.W. Fox, Science, 132, 200 (1960); doi:10.1126/science.132.3421.200.
- J. Wolff, Liebigs Ann., 294, 75 (1850).
- V. Dessaignes, Compt. Rend., 31, 324 (1850).
- K. Harada, H. Mizumoto, K. Ikeda and N. Fujii, Orig. Life, 14, 492 (1986).
- K. Harada, A. Shimoyama and H. Mizumoto, US Patent, No. 4,696,981 (1987).
- K. Harada and H. Mizumoto, J. Biol. Phys., 20, 123 (1995); doi:10.1007/BF00700428.
- M. Bodanszky, Principles of Peptide Synthesis, Springer, Berlin, edn 2 (1993).
- K.J. Jensen A.P. Tofteng and S. L. Pedersen, Peptide Synthesis and Applications (Methods in Molecular Biology) Humana Press, edn 2 (2013).
- A.B. Hughes, Amino Acids, Peptides and Proteins in Organic Chemistry, Building Blocks, Catalysis and Coupling Chemistry (Amino Acids, Peptides and Proteins in Organic Chemistry, Wiley, New York (2011).
- G. Lubec and G. A. Rosenthal, Amino Acids, Kluwer Academic Pub (1992).
- Y-Q. Meng, T. Munegumi and K. Harada, Asian J. Chem, 22, 2738 (2010).
- T. Munegumi, Y-Q. Meng and K. Harada, Chem. Lett., 17, 1643 (1988).
- H. Frank, G.J. Nicholson and E. Bayer, J. Chromatogr. Sci., 15, 174 (1977); doi:10.1093/chromsci/15.5.174.
- H. Frank, G.J. Nicholson and E. Bayer, J. Chromatogr. A, 167, 187 (1978); doi:10.1016/S0021-9673(00)91157-9.
- T. Munegumi and K. Harada, J. Chromatogr. A, 291, 354 (1984); doi:10.1016/S0021-9673(00)95039-8.
References
S.W. Fox, J.E. Johnson and M. Middlebrook, J. Am. Chem. Soc., 77, 1048 (1955); doi:10.1021/ja01609a081.
K. Harada, J. Org. Chem., 24, 1662 (1959); doi:10.1021/jo01093a009.
S.W. Fox, Science, 132, 200 (1960); doi:10.1126/science.132.3421.200.
J. Wolff, Liebigs Ann., 294, 75 (1850).
V. Dessaignes, Compt. Rend., 31, 324 (1850).
K. Harada, H. Mizumoto, K. Ikeda and N. Fujii, Orig. Life, 14, 492 (1986).
K. Harada, A. Shimoyama and H. Mizumoto, US Patent, No. 4,696,981 (1987).
K. Harada and H. Mizumoto, J. Biol. Phys., 20, 123 (1995); doi:10.1007/BF00700428.
M. Bodanszky, Principles of Peptide Synthesis, Springer, Berlin, edn 2 (1993).
K.J. Jensen A.P. Tofteng and S. L. Pedersen, Peptide Synthesis and Applications (Methods in Molecular Biology) Humana Press, edn 2 (2013).
A.B. Hughes, Amino Acids, Peptides and Proteins in Organic Chemistry, Building Blocks, Catalysis and Coupling Chemistry (Amino Acids, Peptides and Proteins in Organic Chemistry, Wiley, New York (2011).
G. Lubec and G. A. Rosenthal, Amino Acids, Kluwer Academic Pub (1992).
Y-Q. Meng, T. Munegumi and K. Harada, Asian J. Chem, 22, 2738 (2010).
T. Munegumi, Y-Q. Meng and K. Harada, Chem. Lett., 17, 1643 (1988).
H. Frank, G.J. Nicholson and E. Bayer, J. Chromatogr. Sci., 15, 174 (1977); doi:10.1093/chromsci/15.5.174.
H. Frank, G.J. Nicholson and E. Bayer, J. Chromatogr. A, 167, 187 (1978); doi:10.1016/S0021-9673(00)91157-9.
T. Munegumi and K. Harada, J. Chromatogr. A, 291, 354 (1984); doi:10.1016/S0021-9673(00)95039-8.