Heating Reactions of N-t-Butyloxycarbonyl-Asparagine and Related Compounds

T. Munegumi; K. Akao; Y. Kawatu; T. Yamada; K. Harada

doi:10.14233/ajchem.2014.16493

Issue

Vol. 26 No. 19 (2014): Vol 26 Issue 19

Issue Published : September 16, 2014

This work is licensed under a Creative Commons Attribution 4.0 International License.

Heating Reactions of N-t-Butyloxycarbonyl-Asparagine and Related Compounds

https://doi.org/10.14233/ajchem.2014.16493

T. Munegumi

Department of Science Education, Naruto University of Education, Naruto, Tokushima 772-8502, Japan; Oyama National College of Technology, Oyama, Tochigi 323-0806, Japan

K. Akao

Department of Chemistry, University of Tsukuba, Tsukuba, Ibaraki 305-8571, Japan

Y. Kawatu

Oyama National College of Technology, Oyama, Tochigi 323-0806, Japan

T. Yamada

Department of Chemistry, University of Tsukuba, Tsukuba, Ibaraki 305-8571, Japan

K. Harada

Department of Chemistry, University of Tsukuba, Tsukuba, Ibaraki 305-8571, Japan

Corresponding Author(s) : T. Munegumi

tmunegumi@naruto-u.ac.jp

Asian Journal of Chemistry, Vol. 26 No. 19 (2014): Vol 26 Issue 19
Article Published : September 19, 2014

Abstract

N-t-Butyloxycarbonyl-amino acids (Boc-) are labile on heating to afford free amino acids, but Boc-aspartic acid gives a kind of polypeptide. This chemical feature of Boc-aspartic acid may be caused by dehydration between two carboxyl groups as well as the formation of a free amino group. Boc-Asparagine may have a similar reactivity to Boc-aspartic acid. This research describes polypeptide formation by heating Boc-asparagine and its isomer Boc-aspartic acid amide.

Keywords

Boc-asparagine Polypeptide Heating reaction

Munegumi, T., Akao, K., Kawatu, Y., Yamada, T., & Harada, K. (2014). Heating Reactions of N-t-Butyloxycarbonyl-Asparagine and Related Compounds. Asian Journal of Chemistry, 26(19), 6541–6548. https://doi.org/10.14233/ajchem.2014.16493

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References

J. Kovacs and H. Nagy, Nature, 191, 531 (1961); doi:10.1038/190531b0.
T. Munegumi, N. Tanikawa, H. Mita and K. Harada, Viva Orig., 22, 109 (1994).
A. Vegotsky, K. Harada and S.W. Fox, J. Am. Chem. Soc., 80, 3361 (1958); doi:10.1021/ja01546a042.
K. Harada, J. Org. Chem., 24, 1662 (1959); doi:10.1021/jo01093a009.
S.W. Fox and K. Harada, J. Am. Chem. Soc., 82, 3745 (1960); doi:10.1021/ja01499a069.
S.W. Fox and K. Harada, Arch. Biochem. Biophys., 86, 281 (1960); doi:10.1016/0003-9861(60)90419-7.
K. Harada and S.W. Fox, Arch. Biochem. Biophys., 86, 274 (1960); doi:10.1016/0003-9861(60)90418-5.
S.W. Fox, Science, 132, 200 (1960); doi:10.1126/science.132.3421.200.
E.A. Talley, T.J. Fitzpatrick and W.L. Porter, J. Am. Chem. Soc., 81, 174 (1959); doi:10.1021/ja01510a040.
J. Bada and S.L. Miller, Biochemistry, 7, 3403 (1968); doi:10.1021/bi00850a014.
J. Bada and S.L. Miller, J. Am. Chem. Soc., 91, 3946 (1969); doi:10.1021/ja01042a047.
J. Bada and S.L. Miller, J. Am. Chem. Soc., 91, 3948 (1969); doi:10.1021/ja01042a048.
J. Bada and S.L. Miller, J. Am. Chem. Soc., 92, 2774 (1970); doi:10.1021/ja00712a031.
T. Munegumi, Y.-Q. Meng and K. Harada, Chem. Lett., 17, 1643 (1988); doi:10.1246/cl.1988.1643.
T. Munegumi, Y.-Q. Meng and K. Harada, Asian J. Chem., 26, 4715 (2014); doi:10.14233/ajchem.2014.16185.
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, 237, 469 (1978).
T. Munegumi and K. Harada, J. Chromatogr. A, 291, 354 (1984); doi:10.1016/S0021-9673(00)95039-8.
E. Schroder and E. Klieger, Ann. Chem., 673, 208 (1964); doi:10.1002/jlac.19646730128.
T. Hayakawa, H. Nishi, J. Noguchi, K. Ikeda, T. Yamashita and T. Isemura, Nippon Kagaku Zasshi, 82, 601 (1961); doi:10.1246/nikkashi1948.82.5_601.
G.W. Anderson and A.C. McGregor, J. Am. Chem. Soc., 79, 6180 (1957); doi:10.1021/ja01580a020.
K.P. Polzhofer, Tetrahedron Lett., 10, 2305 (1969); doi:10.1016/S0040-4039(01)88148-X.
S. Nozaki and I. Muramatsu, Bull. Chem. Soc. Jpn., 61, 2647 (1988); doi:10.1246/bcsj.61.2647.

References

J. Kovacs and H. Nagy, Nature, 191, 531 (1961); doi:10.1038/190531b0.

T. Munegumi, N. Tanikawa, H. Mita and K. Harada, Viva Orig., 22, 109 (1994).

A. Vegotsky, K. Harada and S.W. Fox, J. Am. Chem. Soc., 80, 3361 (1958); doi:10.1021/ja01546a042.

K. Harada, J. Org. Chem., 24, 1662 (1959); doi:10.1021/jo01093a009.

S.W. Fox and K. Harada, J. Am. Chem. Soc., 82, 3745 (1960); doi:10.1021/ja01499a069.

S.W. Fox and K. Harada, Arch. Biochem. Biophys., 86, 281 (1960); doi:10.1016/0003-9861(60)90419-7.

K. Harada and S.W. Fox, Arch. Biochem. Biophys., 86, 274 (1960); doi:10.1016/0003-9861(60)90418-5.

S.W. Fox, Science, 132, 200 (1960); doi:10.1126/science.132.3421.200.

E.A. Talley, T.J. Fitzpatrick and W.L. Porter, J. Am. Chem. Soc., 81, 174 (1959); doi:10.1021/ja01510a040.

J. Bada and S.L. Miller, Biochemistry, 7, 3403 (1968); doi:10.1021/bi00850a014.

J. Bada and S.L. Miller, J. Am. Chem. Soc., 91, 3946 (1969); doi:10.1021/ja01042a047.

J. Bada and S.L. Miller, J. Am. Chem. Soc., 91, 3948 (1969); doi:10.1021/ja01042a048.

J. Bada and S.L. Miller, J. Am. Chem. Soc., 92, 2774 (1970); doi:10.1021/ja00712a031.

T. Munegumi, Y.-Q. Meng and K. Harada, Chem. Lett., 17, 1643 (1988); doi:10.1246/cl.1988.1643.

T. Munegumi, Y.-Q. Meng and K. Harada, Asian J. Chem., 26, 4715 (2014); doi:10.14233/ajchem.2014.16185.

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, 237, 469 (1978).

T. Munegumi and K. Harada, J. Chromatogr. A, 291, 354 (1984); doi:10.1016/S0021-9673(00)95039-8.

E. Schroder and E. Klieger, Ann. Chem., 673, 208 (1964); doi:10.1002/jlac.19646730128.

T. Hayakawa, H. Nishi, J. Noguchi, K. Ikeda, T. Yamashita and T. Isemura, Nippon Kagaku Zasshi, 82, 601 (1961); doi:10.1246/nikkashi1948.82.5_601.

G.W. Anderson and A.C. McGregor, J. Am. Chem. Soc., 79, 6180 (1957); doi:10.1021/ja01580a020.

K.P. Polzhofer, Tetrahedron Lett., 10, 2305 (1969); doi:10.1016/S0040-4039(01)88148-X.

S. Nozaki and I. Muramatsu, Bull. Chem. Soc. Jpn., 61, 2647 (1988); doi:10.1246/bcsj.61.2647.

Issue

Vol. 26 No. 19 (2014): Vol 26 Issue 19

Heating Reactions of N-t-Butyloxycarbonyl-Asparagine and Related Compounds

Corresponding Author(s) : T. Munegumi

Abstract

Keywords

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