Boc/Bzl solid phase synthesis of deltorphin II and its analogues without utilization of anhydrous hydrogen fluoride
- Авторлар: Azev V.N.1, Mustaeva L.G.1, Gorbunova E.Y.1, Baidakova L.K.1, Chulin A.N.1, Maslov L.N.2, Mukhomedziyanov A.V.2, Molchanov М.V.3, Miroshnikov A.I.4
-
Мекемелер:
- Branch of Shemyakin and Ovchinnikov Bioorganic Chemistry Institute RAS
- Cardiology Research Institute, Tomsk National Research Medical Center RAS
- Istitute for Theoretical and Experimental Biophysics RAS
- Shemyakin and Ovchinnikov Bioorganic Chemistry Institute RAS
- Шығарылым: Том 50, № 5 (2024)
- Беттер: 657-664
- Бөлім: Articles
- URL: https://archivog.com/0132-3423/article/view/670805
- DOI: https://doi.org/10.31857/S0132342324050089
- EDN: https://elibrary.ru/LQWVAU
- ID: 670805
Дәйексөз келтіру
Аннотация
The toxicity and aggressive nature of hydrogen fluoride have resulted in development of alternative strong Lewis acid-based reagents for final deprotection and cleavage steps in Boc/Bzl peptide synthesis. The acids employed are high-boiling liquids unlike hydrogen fluoride, however most peptides could be quite easily isolated from the cleavage cocktails due to their favorable physico-chemical properties: they are usually precipitated with ether. We found that this simple procedure is not suitable for the isolation of Deltorphin II peptides and its analogues. Therefore we developed alternative isolation methods and successfully purified these peptides. The procedures developed could be utilized in purification of other hydrophibic peptides.
Негізгі сөздер
Толық мәтін

Авторлар туралы
V. Azev
Branch of Shemyakin and Ovchinnikov Bioorganic Chemistry Institute RAS
Хат алмасуға жауапты Автор.
Email: viatcheslav.azev@bibch.ru
Ресей, prosp. Nauki 6, Puschino, 142290
L. Mustaeva
Branch of Shemyakin and Ovchinnikov Bioorganic Chemistry Institute RAS
Email: viatcheslav.azev@bibch.ru
Ресей, prosp. Nauki 6, Puschino, 142290
E. Gorbunova
Branch of Shemyakin and Ovchinnikov Bioorganic Chemistry Institute RAS
Email: viatcheslav.azev@bibch.ru
Ресей, prosp. Nauki 6, Puschino, 142290
L. Baidakova
Branch of Shemyakin and Ovchinnikov Bioorganic Chemistry Institute RAS
Email: viatcheslav.azev@bibch.ru
Ресей, prosp. Nauki 6, Puschino, 142290
A. Chulin
Branch of Shemyakin and Ovchinnikov Bioorganic Chemistry Institute RAS
Email: viatcheslav.azev@bibch.ru
Ресей, prosp. Nauki 6, Puschino, 142290
L. Maslov
Cardiology Research Institute, Tomsk National Research Medical Center RAS
Email: viatcheslav.azev@bibch.ru
Ресей, ul. Kievskaya 111-A, Tomsk, 634012
A. Mukhomedziyanov
Cardiology Research Institute, Tomsk National Research Medical Center RAS
Email: viatcheslav.azev@bibch.ru
Ресей, ul. Kievskaya 111-A, Tomsk, 634012
М. Molchanov
Istitute for Theoretical and Experimental Biophysics RAS
Email: viatcheslav.azev@bibch.ru
Ресей, ul. Institutskaya 3, Puschino, 142290
A. Miroshnikov
Shemyakin and Ovchinnikov Bioorganic Chemistry Institute RAS
Email: viatcheslav.azev@bibch.ru
Ресей, ul. Miklukho-Maklaya 16/10, Moscow, 117997
Әдебиет тізімі
- Lazarus L.H., Bryant Sh.D., Cooper P.S., Salvadori S. // Prog. Neurobiol. 1999. V. 57. P. 377–420. https://doi.org/10.1016/S0301-0082(98)00050-1
- Headrick J.P., Pepe S., Peart J.N. // Curr. Pharm. Des. 2012. V. 18. P. 6090–6100. https://doi.org/10.2174/138161212803582360
- Rawal H., Patel B.M. // J. Cardiovasc. Pharmacol. Ther. 2018. V. 23. P. 279–291. https://doi.org/10.1177/1074248418757009
- See Hoe L., Patel H.H., Peart J.N. // Delta Opioid Receptors and Cardioprotection. In: Delta Opioid Receptor Pharmacology and Therapeutic Applications. Handbook of Experimental Pharmacology. V. 247 / Ed. Jutkiewicz E. Cham: Springer, 2018. P. 301–334. https://doi.org/10.1007/164_2017_6
- Maslov L.N., Lishmanov Yu.B., Oeltgen P.R., Barzakh E.I., Krylatov A.V., Govindaswami M., Brown S.A. // Life Sci. 2009. V. 84. P. 657–663. https://doi.org/10.1016/j.lfs.2009.02.016
- Maslov L.N., Mukhomedzyanov A.V., Tsibulnikov S.Y., Suleiman M.-S., Khaliulin I., Oeltgen P.R. // Eur. J. Pharmacol. 2021. V. 907. P. 174302. https://doi.org/10.1016/j.ejphar.2021.174302
- Popov S.V., Mukhomedzyanov A.V., Maslov L.N., Naryzhnaya N.V., Kurbatov B.K., Prasad N.R., Singh N., Fu F., Azev V.N. // Membranes. 2023. V. 13. P. 63. https://doi.org/10.3390/membranes13010063
- Salvadori S., Bianchi C., Lazarus L.H., Scaranari V., Attila M., Tomatis R. // J. Med. Chem. 1992. V. 35. P. 4651–4657. https://doi.org/10.1021/jm00103a001
- Benoiton N.L., Lee Y.C., Steinaur R., Chen F.M.F. // Int. J. Pept. Protein Res. 1992. V. 40. P. 559–566. https://doi.org/10.1111/j.1399-3011.1992.tb00441.x
- Yang Y. // Side Reactions in Peptide Synthesis (1st ed.). London: Academic Press, 2015.
- Guerrini R., Capasso A., Sorrentino L., Anacardio R., Bryant Sh.D., Lazarus L.H., Attila M., Salvadori S. // Eur. J. Pharmacol. 1996. V. 302. P. 37–42. https://doi.org/10.1016/0014-2999(96)00067-2
- Sakakibara S., Nakamizo N., Kishida Y., Yoshimura S. // Bull. Chem. Soc. Jpn. 1968. V. 41. P. 1477–1479. https://doi.org/10.1246/bcsj.41.1477
- Muttenthaler M., Albericio F., Dawson P.E. // Nat. Protoc. 2015. V. 10. P. 1067–1083. https://doi.org/10.1038/nprot.2015.061
- Hughes J.L., Leopold E.J. // Tetrahedron Lett. 1993. V. 34. P. 7713–7716. https://doi.org/10.1016/S0040-4039(00)61546-0
- Akaji K., Fujii N., Tokunaga F., Miyata T., Iwanaga S., Yajima H. // Chem. Pharm. Bull. 1989. V. 37. P. 2661– 2664. https://doi.org/10.1248/cpb.37.2661
- Jubilut G.N., Cilli E.M., Tominaga M., Miranda A., Okada Y., Nakaie C.R. // Chem. Pharm. Bull. 2001. V. 49. P. 1089–1092. https://doi.org/10.1248/cpb.49.1089
- Schnölzer M., Alewood P., Jones A., Alewood D., Kent S.B.H. // Int. J. Pept. Protein Res. 1992. V. 40. P. 180–193. https://doi.org/10.1111/j.1399-3011.1992.tb00291.x
- Kaiser E., Colescott R.L., Bossinger C.D., Cook P.I. // Anal. Biochem. 1970. V. 34. P. 595. https://doi.org/10.1016/0003-2697(70)90146-6
- Stewart J.M., Young J.D. // Solid Phase Peptide Synthesis. Pierce Chemical Company Rockford, IL, 1984.
- Yajima H., Fujii N. // J. Am. Chem. Soc. 1981. V. 103. P. 5867–5871. https://doi.org/10.1021/ja00409a040
- Kravchenko S.V., Domnin P.A., Grishin S.Yu., Panfilov A.V., Azev V.N., Mustaeva L.G., Gorbunova E.Yu., Kobyakova M.I., Surin A.K., Glyakina A.V., Fadeev R.S., Ermolaeva S.A., Galzitskaya O.V. // Int. J. Mol. Sci. 2022. V. 23. P. 524. https://doi.org/10.3390/ijms23010524
- Espada A., Rivera-Sagredo A. // J. Chromatogr. A. 2003. V. 987. P. 211–220. https://doi.org/10.1016/S0021-9673(02)01819-8
- Subirats X., Bosch E., Rosés M. // LCGC North America. 2009. V. 27. P. 1000–1004. https://www.chromatographyonline.com/view/buffer-considerations-lc-and-lc-ms
- Göransson U., Luijendijk T., Johansson S., Bohlin L., Claeson P. // J. Nat. Prod. 1999. V. 62. P. 283–286. https://doi.org/10.1021/np9803878
- Barbeau D., Guay S., Neugebauer W., Escher E. // J. Med. Chem. 1992. V. 35. P. 151–157. https://doi.org/10.1021/jm00079a020
- Myhre P.C. // J. Am. Chem. Soc. 1972. V. 94. P. 7921–7923. https://doi.org/10.1021/ja00777a043
- Olah G.A., Narang S.C., Malhotra R., Olah J.A. // J. Am. Chem. Soc. 1979. V. 101. P. 1805–1807. https://doi.org/10.1021/ja00501a028
- Nickson T.E. // J. Org. Chem. 1986. V. 51. P. 3903– 3904. https://doi.org/10.1021/jo00370a031
- Shiao M.-J., Lai L.-L., Ku W.-Sh., Lin P.-Y., Hwu J. R. // J. Org. Chem. 1993. V. 58. P. 4742–4744. https://doi.org/10.1021/jo00069a046
- Knorr R., Trzeciak A., Bannwarth W., Gillessen D. // Tetrahedron Lett. 1989. V. 30. P. 1927–1930. https://doi.org/10.1016/S0040-4039(00)99616-3
Қосымша файлдар
