Regiospecific Preparation of a Suitably Protected β-Branched Aspartic Acid Dipeptide

Capa

Citar

Texto integral

Acesso aberto Acesso aberto
Acesso é fechado Acesso está concedido
Acesso é fechado Somente assinantes

Resumo

A new efficient synthetic approach for the preparation of Nα-protected β-L-aspartyl-L-aspartic acid dipeptide was elaborated. The distinctive features of the developed approach include utilization of readily available starting materials (Cbz-asparagine and dimethyl aspartate), aspartimide formation suppression employing electrostatic effect in a final deprotection step and an employment of a novel reagent (NaNO2/aqueous trifluoroacetic acid) for transformation of protected asparagine derivative into the corresponding aspartic acid. The developed method allowes preparation of aspartic acid derivatives that find application in carbohydrate polivalent interaction studies as well as in preparation of microbicidal dendrimeric constructs.

Sobre autores

V. Azev

Branch of Shemyakin and Ovchinnikov Bioorganic Chemistry Institute, RAS

Autor responsável pela correspondência
Email: viatcheslav.azev@bibch.ru
Russia, 142290, Pushchino, prosp. Nauki 6

L. Baidakova

Branch of Shemyakin and Ovchinnikov Bioorganic Chemistry Institute, RAS

Email: viatcheslav.azev@bibch.ru
Russia, 142290, Pushchino, prosp. Nauki 6

A. Chulin

Branch of Shemyakin and Ovchinnikov Bioorganic Chemistry Institute, RAS

Email: viatcheslav.azev@bibch.ru
Russia, 142290, Pushchino, prosp. Nauki 6

A. Tuzikov

Shemyakin-Ovchinnikov Bioorganic Chemistry Institute, RAS

Email: viatcheslav.azev@bibch.ru
Russia, 117997, Moscow, ul. Miklukho-Maklaya 16/10

P. Kislitsyn

CHEMRAR Group

Email: viatcheslav.azev@bibch.ru
Russia, 141401, Khimki, ul. Rabochaya 2a-1

M. Molchanov

Institute for Theoretical and Experimental Biophysics, RAS

Email: viatcheslav.azev@bibch.ru
Russia, 142290, Pushchino, ul. Institutskaya 3

A. Miroshnikov

Shemyakin-Ovchinnikov Bioorganic Chemistry Institute, RAS

Email: viatcheslav.azev@bibch.ru
Russia, 117997, Moscow, ul. Miklukho-Maklaya 16/10

Bibliografia

  1. Müller Ch., Despras G., Lindhorst T.K. // Chem. Soc. Rev. 2016. V. 45. P. 3275–3302. https://doi.org/10.1039/C6CS00165C
  2. Korchagina E.Y., Henry S.M. // Biochemistry (Moscow). 2015. V. 80. P. 857–871. https://doi.org/10.1134/S0006297915070068
  3. Петракова Д.О., Савченко М.С., Попова И.С., Тузиков А.Б., Парамонов А.С., Чижов А.О., Бовин Н.В., Рыжов И.М. // Биоорг. химия. 2023. Т. 49. № 4. С. 422–433. https://doi.org/10.31857/S013234232304036X
  4. Le Quesne W.J., Young G.T. // J. Chem. Soc. 1952. P. 24–28. https://doi.org/10.1039/JR9520000024
  5. Lee R.T., Lin P., Lee Yu.C. // Biochemistry. 1984. V. 23. P. 4255–4261. https://doi.org/10.1021/bi00313a037
  6. Lee R.T., Lee Yu.C. // Bioconjug. Chem. 1997. V. 8. P. 762–765. https://doi.org/10.1021/bc9700796
  7. Benoiton N.L., Chen F.M.F., Steinauer R., Chouinard M. // Int. J. Peptide Protein Res. 1986. V. 27. P. 28–33. https://doi.org/10.1111/j.1399-3011.1986.tb02762.x
  8. Itoh M.I. // Chem. Pharm. Bull. 1969. V. 17. P. 1679–1686. https://doi.org/10.1248/cpb.17.1679
  9. Ledger R., Stewart F.H.C. // Aust. J. Chem. 1965. V. 18. P. 1477–1484. https://doi.org/10.1071/CH9651477
  10. Nefkens G.H.L., Zwanenburg B. // Tetrahedron. 1983. V. 39. P. 2995–2998. https://doi.org/10.1016/S0040-4020(01)92162-3
  11. Pumpor K., Windeisen E., Spengler J., Albericio F., Burger K. // Monatsh. Chem. 2004. V. 135. P. 1427–1443. https://doi.org/10.1007/s00706-004-0183-9
  12. Mehrotra A.P., Webster K.L., Gani D. // J. Chem. Soc. Perkin Trans. 1. 1997. P. 2495–2512. https://doi.org/10.1039/A702407J
  13. Sánchez A., Calderón E., Vazquez A. // Synthesis. 2013. V. 45. P. 1364–1372. https://doi.org/10.1055/s-0032-1316848
  14. Subirós-Funosas R., El-Faham A., Albericio F. // Tetrahedron. 2011. V. 45. P. 8595–8606. https://doi.org/10.1016/j.tet.2011.08.046
  15. Roeske R. // J. Org. Chem. 1963. V. 28. P. 1251–1253. https://doi.org/10.1021/jo01040a022
  16. Abell A.D., Edwards R.A., Oldham M.D. // J. Chem. Soc. Perkin Trans. 1. 1997. P. 1655–1662. https://doi.org/10.1039/A608165G
  17. Gregory H., Morley J.S., Smith J.M., Smithers M.J. // J. Chem. Soc. 1968. P. 715–725. https://doi.org/10.1039/J39680000715
  18. Isidro-Llobet A., Álvarez M., Albericio F. // Chem Rev. 2009. V. 109. P. 2455–2504. https://doi.org/10.1021/cr800323s
  19. Nefkens G.H.L., Nivard R.J.F. // Recl. Trav. Chim. Pays-Bas. 1965. V. 84. P. 1315–1318. https://doi.org/10.1002/recl.19650841013
  20. Sondheimer E., Semeraro R.J. // J. Org. Chem. 1961. V. 26. P. 1847–1849. https://doi.org/10.1021/jo01065a038
  21. Cosmatos A., Johnson S., Breier B., Katsoyannis P.G. // J. Chem. Soc. Perkin Trans. 1. 1975. P. 2157–2163. https://doi.org/10.1039/P19750002157
  22. Schoutissen H.A.J. // J. Am. Chem. Soc. 1933. V. 55. P. 4531–4534. https://doi.org/10.1021/ja01338a032
  23. Hodgson H.H., Mahadevan A.P., Ward E.R. // Org. Synth. 1948. V. 28. P. 52–54. https://doi.org/10.1002/0471264180.os028.21
  24. Moss R.A., Bracken K., Emge T.J. // J. Org. Chem. 1995. V. 60. P. 7739–7746. https://doi.org/10.1021/jo00129a012
  25. Anzeveno P.B., Creemer L.J., Daniel J.K., King C.H.R., Liu P.S. // J. Org. Chem. 1989. V. 54. P. 2539–2542. https://doi.org/10.1021/jo00272a015
  26. Hendrickson J.B., Kandall C. // Tetrahedron Lett. 1970. V. 11. P. 343–344. https://doi.org/10.1016/0040-4039(70)80079-X
  27. Suzuki K., Endo N.T. // Chem. Pharm. Bull. 1978. V. 26. P. 2269–2274. https://doi.org/10.1248/cpb.26.2269
  28. Neumann K., Farnung J., Baldauf S., Bode J.W. // Nature Commun. 2020. V. 11. P. 982. https://doi.org/10.1038/s41467-020-14755-6
  29. Adang A.E., Duindam A.J., Brussee J., Mulder G.J., Van Der Gen A. // Biochem. J. 1988. V. 255. P. 715. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1135284/
  30. Gleich A., Schmidtcher F.P., Scheuplein S.W., Kusche A., Brückner R., Harms K. // Chem. Ber. 1990. V. 123. P. 907–915. https://doi.org/10.1002/cber.19901230442
  31. Niggemann M., Ritter H. // Acta Polym. 1996. V. 47. P. 351–356. https://doi.org/10.1002/actp.1996.010470806
  32. Akbari A., Bigham A., Rahimkhoei V., Sharifi S., Jabbari A. // Polymers. 2022. V. 14. P. 1634. https://doi.org/10.3390/polym14091634
  33. Armarego W.L.F., Chai C. // Purification of Laboratory Chemicals, 6th ed. Oxford: Butterworth-Heinemann, 2012.
  34. Gmeiner P., Feldman P.L., Chu-Moyer M.Y., Rapoport H. // J. Org. Chem. 1990. V. 55. P. 3068–3074. https://doi.org/10.1021/jo00297a023
  35. Benassi R., Folli U., Schenetti L., Taddei F. // Adv. Het. Chem. 1987. V. 41. P. 75–186. https://doi.org/10.1016/S0065-2725(08)60161-0

Arquivos suplementares

Arquivos suplementares
Ação
1. JATS XML
Baixar
2.

Baixar (81KB)
Metadados
3.

Baixar (173KB)
Metadados
4.

Baixar (98KB)
Metadados
5.

Baixar (108KB)
Metadados
6.

Baixar (68KB)
Metadados

Declaração de direitos autorais © В.Н. Азев, Л.К. Байдакова, А.Н. Чулин, А.Б. Тузиков, П.Г. Кислицин, М.В. Молчанов, А.И. Мирошников, 2023