Copyright (c) 2015 AJC
This work is licensed under a Creative Commons Attribution 4.0 International License.
Carboxyl Activation of 2-Mercapto-4,6-dimethylpyrimidine through N-Acyl-4,6-dimethylpyrimidine-2-thione: A Chemical and Spectrophotometric Investigation
Corresponding Author(s) : M.P. Rajan
Asian Journal of Chemistry,
Vol. 27 No. 1 (2015): Vol 27 Issue 1
Abstract
2-Mercapto-4,6-dimethylpyrimidine, as effective carboxyl activating group, has been successfully proved by converting it into respective acyl derivatives and the subsequent conversion to the amides and esters respectively using amines, amino alcohols and alcohols. The aminolysis and esterification were monitored chemically and spectrophotometrically. This paved way to establish that the above mercaptopyrimidine derivative is an efficient carboxyl activating group applicable in solid phase peptide synthesis.
Keywords
Download Citation
Endnote/Zotero/Mendeley (RIS)BibTeX
- I.J. Galpin, Amino Acids, Peptides and Proteins, The Royal Society of Chemistry, Burlington House, London, Vol. 16, p. 272 (1985).
- B.J. Reinhart and D.P. Bartel, Science, 297, 1831 (2002); doi:10.1126/science.1077183.
- Y.X. Fu and D.D. Chaplin, Annu. Rev. Immunol., 17, 399 (1999); doi:10.1146/annurev.immunol.17.1.399.
- Y. Wang, G. Huang, J. Wang, H. Molina, D.D. Chaplin and Y.-X. Fu, Eur. J. Immunol., 30, 2226 (2000); doi:10.1002/1521-4141(2000)30:8<2226::AID-IMMU2226>3.0.CO;2-5.
- Y. Takahashi, H. Ohta and T. Takemori, Immunity, 14, 181 (2001); doi:10.1016/S1074-7613(01)00100-5.
- N.L. Dayneka, V. Garg and W.J. Jusko, J. Pharmacokinet. Biopharm., 21, 457 (1993).
- C.R. Craig and R.E. Stitzel, Modern Pharmacology, Little Brown & Co., Boston, edn 3 (1990).
- A.N. Lane and K. Kirschner, Eur. J. Biochem., 129, 571 (1983); doi:10.1111/j.1432-1033.1983.tb07087.x.
- H. Zalkin and C. Yanofsky, J. Biol. Chem., 257, 1491 (1982).
- L.C. Packman and R.N. Perham, Biochem. J., 242, 531 (1987).
- C.A. Bently and K.F. Lee, J. Neurosci., 20, 7706 (2000).
- E.J. Huang and L.F. Reichardt, Annu. Rev. Neurosci., 24, 677 (2001); doi:10.1146/annurev.neuro.24.1.677.
- M.P Rajan and E. Purushothaman, Protein Peptide Lett., 15, 1068 (2008); doi:10.2174/092986608786071148.
- M.P. Rajan, Asian J. Chem., 21, 7327 (2009).
- M.P. Rajan and E. Purushothaman, Indian J. Heterocycl. Chem., 12, 71 (2002).
- E. Purushothaman, M.P. Rajan and T.T. Marykutty, Indian J. Heterocycl. Chem., 11, 43 (2001).
- S.H. Pine, J.B. Hendrickson, D.J. Cram and G.S. Hammond, Organic Chemistry, McGraw-Hill Int. Book Co., Japan (1982).
- G. Petrillo, M. Novi, G. Garbarino and M. Filiberti, Tetrahedron, 45, 7411 (1989); doi:10.1016/S0040-4020(01)89203-6.
- R. Berenguer, J. Garcia and J. Vilarrasa, Synthesis, 305 (1989);doi:10.1055/s-1989-27234.
- S. Antebi and H. Alper, Organometallics, 5, 596 (1986); doi:10.1021/om00134a038.
- Y. Oishi, M. Tanaka, M. Kakimoto and Y. Imai, Makromol. Chem., Rapid Commun., 12, 465 (1991); doi:10.1002/marc.1991.030120802.
- M.F. El-Zohry, A.M. El-Khawaga, M.T. Ismail and A.A. Abdel-Wahab, Phosphorus Sulfur Silicon Rel. Elem., 61, 373 (1991); doi:10.1080/10426509108036820.
- C.L Joshy and E. Purushothaman, Proc. Indian Acad. Sci: (Chem. Sci.), 104, 773 (1992).
- E. Purushothaman, Indian J. Heterocycl. Chem, 7, 93 (1997).
- V.N.R. Pillai, Synthesis, 1 (1980); doi:10.1055/s-1980-28908.
- V.N. Rajasekharan Pillai, M. Mutter and E. Bayer, Tetrahedron Lett., 20, 3409 (1979); doi:10.1016/S0040-4039(01)95422-X.
- H.H. Wasserman, R.J. Gambale and M.J. Pulwer, Tetrahedron Lett., 22, 1737 (1981); doi:10.1016/S0040-4039(01)90426-5.
- H.H. Wasserman and T.J. Lu, Tetrahedron Lett., 23, 3831 (1982); doi:10.1016/S0040-4039(00)87719-9.
- R.W. Binkley, J. Org. Chem., 41, 3030 (1976); doi:10.1021/jo00880a024.
- R.W. Binkley, J. Org. Chem., 42, 1216 (1977); doi:10.1021/jo00427a025.
- B. Kumar, H. Kumar and S. Arora, Indian J. Chem. 32B, 779 (1993).
- H.J. Sanders, Chem. Eng. News, 59, 20 (1981); doi:10.1021/cen-v059n031.p020.
- G. Levitt, et al., U.S. Patent, 4,905 (1978).
- G. Levitt, H.L. Ploeg, R.C. Weigel and D.J. Fitzgerald, J. Agric. Food Chem., 29, 416 (1981); doi:10.1021/jf00104a049.
- T. Ray, Proc. British Crop Protection Conference Veeds, 1, 7 (1982).
- T. Ray, Pestic. Biochem. Physiol., 17, 10 (1982); doi:10.1016/0048-3575(82)90120-1.
- H. Westlinning, Rubber Chem. Technol., 43, 1194 (1970); doi:10.5254/1.3547318.
- K.H. Kim, S.W. Dietrich, C. Hansch, B.J. Dolnick and J.R. Bertino, J. Med. Chem., 23, 1248 (1980);doi:10.1021/jm00185a022.
- A.J. Hopfinger, J. Am. Chem. Soc., 102, 7196 (1980); doi:10.1021/ja00544a005.
- R. Brehme, B. Storede, A. Klemannm, U. Foellmer, J. Bohrisch, E. Gruendeman and H. Becker, Gem (East) DD, 220, 956 (1989).
- A.I. Vogel, Text book of Practical Organic Chemistry, ELBS and Longmann, London, edn. 4 (1980).
- J.W. Grasselli and W.M. Ritchey, Atlas of Spectral Data and Physical Constants for Organic Compounds, CRC Press Inc., edn. 2, Vol. 1-6 (1975).
- G.L. Clark, The Encyclopaedia of Chemistry, Eyre and Van Nostrand Reinhold Company, New York (1966).
- P. Beak, F.S. Fry, J. Lee and F. Steele, J. Am. Chem. Soc., 98, 171 (1976); doi:10.1021/ja00417a027.
References
I.J. Galpin, Amino Acids, Peptides and Proteins, The Royal Society of Chemistry, Burlington House, London, Vol. 16, p. 272 (1985).
B.J. Reinhart and D.P. Bartel, Science, 297, 1831 (2002); doi:10.1126/science.1077183.
Y.X. Fu and D.D. Chaplin, Annu. Rev. Immunol., 17, 399 (1999); doi:10.1146/annurev.immunol.17.1.399.
Y. Wang, G. Huang, J. Wang, H. Molina, D.D. Chaplin and Y.-X. Fu, Eur. J. Immunol., 30, 2226 (2000); doi:10.1002/1521-4141(2000)30:8<2226::AID-IMMU2226>3.0.CO;2-5.
Y. Takahashi, H. Ohta and T. Takemori, Immunity, 14, 181 (2001); doi:10.1016/S1074-7613(01)00100-5.
N.L. Dayneka, V. Garg and W.J. Jusko, J. Pharmacokinet. Biopharm., 21, 457 (1993).
C.R. Craig and R.E. Stitzel, Modern Pharmacology, Little Brown & Co., Boston, edn 3 (1990).
A.N. Lane and K. Kirschner, Eur. J. Biochem., 129, 571 (1983); doi:10.1111/j.1432-1033.1983.tb07087.x.
H. Zalkin and C. Yanofsky, J. Biol. Chem., 257, 1491 (1982).
L.C. Packman and R.N. Perham, Biochem. J., 242, 531 (1987).
C.A. Bently and K.F. Lee, J. Neurosci., 20, 7706 (2000).
E.J. Huang and L.F. Reichardt, Annu. Rev. Neurosci., 24, 677 (2001); doi:10.1146/annurev.neuro.24.1.677.
M.P Rajan and E. Purushothaman, Protein Peptide Lett., 15, 1068 (2008); doi:10.2174/092986608786071148.
M.P. Rajan, Asian J. Chem., 21, 7327 (2009).
M.P. Rajan and E. Purushothaman, Indian J. Heterocycl. Chem., 12, 71 (2002).
E. Purushothaman, M.P. Rajan and T.T. Marykutty, Indian J. Heterocycl. Chem., 11, 43 (2001).
S.H. Pine, J.B. Hendrickson, D.J. Cram and G.S. Hammond, Organic Chemistry, McGraw-Hill Int. Book Co., Japan (1982).
G. Petrillo, M. Novi, G. Garbarino and M. Filiberti, Tetrahedron, 45, 7411 (1989); doi:10.1016/S0040-4020(01)89203-6.
R. Berenguer, J. Garcia and J. Vilarrasa, Synthesis, 305 (1989);doi:10.1055/s-1989-27234.
S. Antebi and H. Alper, Organometallics, 5, 596 (1986); doi:10.1021/om00134a038.
Y. Oishi, M. Tanaka, M. Kakimoto and Y. Imai, Makromol. Chem., Rapid Commun., 12, 465 (1991); doi:10.1002/marc.1991.030120802.
M.F. El-Zohry, A.M. El-Khawaga, M.T. Ismail and A.A. Abdel-Wahab, Phosphorus Sulfur Silicon Rel. Elem., 61, 373 (1991); doi:10.1080/10426509108036820.
C.L Joshy and E. Purushothaman, Proc. Indian Acad. Sci: (Chem. Sci.), 104, 773 (1992).
E. Purushothaman, Indian J. Heterocycl. Chem, 7, 93 (1997).
V.N.R. Pillai, Synthesis, 1 (1980); doi:10.1055/s-1980-28908.
V.N. Rajasekharan Pillai, M. Mutter and E. Bayer, Tetrahedron Lett., 20, 3409 (1979); doi:10.1016/S0040-4039(01)95422-X.
H.H. Wasserman, R.J. Gambale and M.J. Pulwer, Tetrahedron Lett., 22, 1737 (1981); doi:10.1016/S0040-4039(01)90426-5.
H.H. Wasserman and T.J. Lu, Tetrahedron Lett., 23, 3831 (1982); doi:10.1016/S0040-4039(00)87719-9.
R.W. Binkley, J. Org. Chem., 41, 3030 (1976); doi:10.1021/jo00880a024.
R.W. Binkley, J. Org. Chem., 42, 1216 (1977); doi:10.1021/jo00427a025.
B. Kumar, H. Kumar and S. Arora, Indian J. Chem. 32B, 779 (1993).
H.J. Sanders, Chem. Eng. News, 59, 20 (1981); doi:10.1021/cen-v059n031.p020.
G. Levitt, et al., U.S. Patent, 4,905 (1978).
G. Levitt, H.L. Ploeg, R.C. Weigel and D.J. Fitzgerald, J. Agric. Food Chem., 29, 416 (1981); doi:10.1021/jf00104a049.
T. Ray, Proc. British Crop Protection Conference Veeds, 1, 7 (1982).
T. Ray, Pestic. Biochem. Physiol., 17, 10 (1982); doi:10.1016/0048-3575(82)90120-1.
H. Westlinning, Rubber Chem. Technol., 43, 1194 (1970); doi:10.5254/1.3547318.
K.H. Kim, S.W. Dietrich, C. Hansch, B.J. Dolnick and J.R. Bertino, J. Med. Chem., 23, 1248 (1980);doi:10.1021/jm00185a022.
A.J. Hopfinger, J. Am. Chem. Soc., 102, 7196 (1980); doi:10.1021/ja00544a005.
R. Brehme, B. Storede, A. Klemannm, U. Foellmer, J. Bohrisch, E. Gruendeman and H. Becker, Gem (East) DD, 220, 956 (1989).
A.I. Vogel, Text book of Practical Organic Chemistry, ELBS and Longmann, London, edn. 4 (1980).
J.W. Grasselli and W.M. Ritchey, Atlas of Spectral Data and Physical Constants for Organic Compounds, CRC Press Inc., edn. 2, Vol. 1-6 (1975).
G.L. Clark, The Encyclopaedia of Chemistry, Eyre and Van Nostrand Reinhold Company, New York (1966).
P. Beak, F.S. Fry, J. Lee and F. Steele, J. Am. Chem. Soc., 98, 171 (1976); doi:10.1021/ja00417a027.