Abstract
A chemo-enzymatic method is proposed for the preparation of (S,S)-2,2′-(ethylenediamino)dibutan-1-ol based on the synthesis of racemic (±)-N-carbobenzoxy-2-amino-butan-1-ol and its enantioselective acylation in the presence of lipase at a key resolution step to release the optically active alcohol.
References
Beena, D. S. Rawat, Med. Res. Rev., 2013, 33, 693; DOI: https://doi.org/10.1002/med.21262.
O. Danilchanka, M. Pavlenok, M. Niederweis, Antimicrob. Agents Chemother., 2008, 52, 3127; DOI: https://doi.org/10.1128/AAC.00239-08.
S. Filatova, O. V. Fedorova, I. G. Ovchinnikova, K. A. Chistyakov, G. L. Rusinov, V. N. Charushin, Russ. Chem. Bull., 2022, 71, 1506; DOI: https://doi.org/10.1007/s11172-022-3557-4.
R. I. Ishmetova, I. N. Ganebnykh, N. K. Ignatenko, S. G. Tolshchina, A. V. Korotina, O. S. Eltsov, M._A. Kravchenko, G. L. Rusinov, Russ. Chem. Bull., 2021, 70, 1093; DOI: https://doi.org/10.1007/s11172-021-3189-0.
R. Yendapally, R. E. Lee, Bioorg. Med. Chem. Lett., 2008, 18, 1607; DOI: https://doi.org/10.1016/j.bmcl.2008.01.065.
M. V. Mavrov, N. I. Simirskaya, Pharm. Chem. J., 2013, 46, 730; DOI: https://doi.org/10.1007/s11094-013-0880-y.
A. V. Omel’kov, V. E. Fedorov, A. A. Stepanov, Russ. Chem. Bull., 2019, 68, 1908; DOI: https://doi.org/10.1007/s11172-019-2646-5.
C. Aguilar-Pérez, B. Gracia, L. Rodrigues, A. Vitoria, R. Cebrián, N. Deboosère, Ok-r. Song, P. Brodin, M. Maqueda, J. A. Aínsaa, Antimicrob. Agents Chemother., 2013, 62, e00359–18; DOI: https://doi.org/10.1128/AAC.00359-18.
H.-J. Kim, J. S. Lee, N. Kwak, J. Cho, C.-H. Lee, S. K. Han, J.-J. Yim, BMC Pulmon. Med., 2019, 19, Art. No. 212; DOI: https://doi.org/10.1186/s12890-019-0982-8.
M. D. Mashkovsii, Lekarstvennye Sredstva [Pharmaceutical Products], 15th ed., Novaya Volna, Moscow, 2008, pp. 861–862 (in Russian).
L. Zhao, Q. Sun, H. Liu, X. Wu, T. Xiao, X. Zhao, G. Li, Y. Jiang, C. Zeng, K. Wan, Antimicrob. Agents Chemother., 2015, 59, 2045; DOI: https://doi.org/10.1128/aac.04933-14.
D. Kulig, Z. Bugielska, K. Rokicka, Diss. Pharm. Pharmacol., 1971, 22, 463
D. Kulig, Z. Bugielska, K. Rokicka, Chem. Absr., 1972, 76, 81239.
R. G. Wilkinson, M. B. Cantrall, R. G. Shepherd, J. Med. Pharm. Chem., 1962, 5, 835; DOI: https://doi.org/10.1021/jm01239a018.
X. Xiang, Z. Gong, W. Deng, Q. Sun, J. Xie, J. Drug Targeting, 2020, 29, 284; DOI: https://doi.org/10.1080/1061186x.2020.1853733.
W.-Y. Sheng, Sh.-Q. Wu, L.-Y. Su, L.-W. Zhu, World J. Clin. Cases, 2022, 10, 663; DOI: https://doi.org/10.12998/wjcc.v10.i2.663.
R. G. Wilkinson, R. G. Shepherd, J. P. Thomas, C. Baughn, J. Am. Chem. Soc., 1961, 83, 2212; DOI: https://doi.org/10.1021/JA01470A052.
Pat. SU 522792, 1977.
Pat. US 3944618A, 1976.
Pat. SU 498902, 1976.
M. Breuer, K. Ditrich, T. Habicher, B. Hauer, M. Keßeler, R. Stürmer, T. Zelinski, Angew. Chem., Int. Ed., 2004, 43, 788; DOI: https://doi.org/10.1002/anie.200300599.
Yu. N. Belokon’, N. I. Chernoglazova, K. A. Kochetkov, N. S. Garbalinskaya, M. G. Ryzhov, V. I. Bakhmutov, M. B. Saporovskaya, E. A. Paskonova, V. I. Maleev, S. V. Vitt, V. M. Belikov, Russ. Chem. Bull., 1984, 33, 738; DOI: https://doi.org/10.1007/BF00947824.
B. M. Trost, R. C. Bunt, R. C. Lemoine, T. L. Calkins, J. Am. Chem. Soc., 2000, 122, 5968; DOI: https://doi.org/10.1021/JA000547D.
C. S. Stauffer, A. Datta, Tetrahedron, 2002, 58, 9765; DOI: https://doi.org/10.1016/S0040-4020(02)01308-X.
R. S. B. Goncalves, E. T. da Silva, M. V. N. de Souza, Lett. Org. Chem., 2015, 12, 478; DOI: https://doi.org/10.2174/1570178612666150521235908.
S. P. Kotkar, A. Sudalai, Tetrahedron: Asymmetry, 2006, 17, 1738; DOI: https://doi.org/10.1016/J.TETASY.2006.06.011.
R. O. M. A. de Souza, R. Aguiar, R. A. C. Leão, L. S. M. Miranda, C. O. Kappe, D. Cantillo, A. Mata, Org. Biomol. Chem., 2019, 10, 1039; DOI: https://doi.org/10.1039/C8OB03088J.
B. Saifullah, A. Chrzastek, A. Maitra, B. Naeemullah, S. Fakurazi, S. Bhakta, M. Hussein, Molecules, 2017, 22, 1560; DOI: https://doi.org/10.3390/molecules22101560.
E. Nemati, A. Mokhtarzadeh, V. Panahi-Azar, A. Mohammadi, H. Hamishehkar, M. Mesgari-Abbasi, J. E. N. Dolatabadi, M. de la Guardia, AAPS PharmSciTech., 2019, 20, Art. No. 120; DOI: https://doi.org/10.1208/s12249-019-1334-y.
Y. Lv, C. Tang, J. Liao, S. Wu, L. Yao, H. Ruan, A. Sotto, J. Shen, ACS Sustain. Chem. Eng., 2021, 9, 3542; DOI: https://doi.org/10.1021/acssuschemeng.0c08540.
K. A. Kochetkov, M. A. Galkina, O. M. Galkin, Mendeleev Commun., 2010, 20, 314; DOI: https://doi.org/10.1016/j.mencom.2010.11.003.
S. Fernandes, R. Brieva, F. Reboleddo, V. Gotor, J. Chem. Soc., Perkin Trans. 1, 1992, 2885; DOI: https://doi.org/10.1039/P19920002885.
A. Maestro, C. Astorga, V. Gotor, Tetrahedron Asymmetry, 1997, 8, 3153; DOI: https://doi.org/10.1016/S0957-4166(97)00368-6.
P. Kumar, V. Naidu, P. Gupta, Tetrahedron, 2007, 63, 2745; DOI: https://doi.org/10.1016/j.tet.2006.12.015.
A. O. Kolodiazhna, O. V. Veriovka, O. I. Kolodiazhnyi, Dopov. Nats. Akad. Nauk Ukr., 2019, No. 8, 78; DOI: https://doi.org/10.15407/dopovidi2019.08.078.
R. J. Kazlauskas, U. T. Bornscheuer, Hydrolases in Organic Synthesis, 2nd ed., VCH, Weinhein, 2006, pp. 61–183.
A. Kamal, G. B. R. Khanna, R. Ramu, T. Krishnaji, Tetrahedron Lett., 2003, 44, 4783; DOI: https://doi.org/10.1016/S0040-4039(03)00945-6.
F. M. Plieva, K. A. Kochetkov, I. Singh, V. S. Parmar, Y. N. Belokon, V. I. Lozinsky, Biotechnol. Lett., 2000, 22, 551; DOI: https://doi.org/10.1023/A:1005660125927.
Y. N. Belokon, K. A. Kochetkov, E. N. Baranova, D. Poncelet, V. Parmar, R. Kumar, V. P. Zubov, D. Rumsh, Appl. Biochem. Biotechnol., 2000, 88, 145; DOI: https://doi.org/10.1385/ABAB:88:1-3:145.
N. G. Faleev, M. A. Tsvetikova, M. M. Ilyin, V. S. Yufryakov, N. G. Kolotyrkina, V. V. Kulikova, T. V. Demidkina, K. A. Kochetkov, Mendeleev Commun., 2021, 31, 236; DOI: https://doi.org/10.1016/j.mencom.2021.03.030.
Pat. RU 2712231, 2020.
E. T. Pelkey, G. W. Gribble, Can. J. Chem., 2006, 84, 1338; DOI: https://doi.org/10.1139/V06-075.2.
C. Zhu, M.-Y. Han, X.-X. Liang, B. Guan, P. Li, L. Wang, Org. Lett., 2021, 23, 54; DOI: https://doi.org/10.1021/acs.orglett.0c03683.
B. I. Morinaka, M. N. Masuno, J. R. Pawlik, T. F. Molinski, Org. Lett., 2007, 9, 5219; DOI: https://doi.org/10.1021/ol702325e.
P. G. M. Wuts, T. W. Greene, Greene’s Protective Groups in Organic Synthesis, 4th ed., Wiley, 2007, p. 1100.
The Merck Index. An Encyclopedia of Chemicals, Drugs, and Biologicals, Ed. M. J. O’Neil, 14th ed., Merck & Co., Inc., USA, 2006, p. 638.
Author information
Authors and Affiliations
Corresponding author
Additional information
This work was financially supported by the Ministry of Science and Higher Education of the Russian Federation (State Task No. 075-00697-22-00). The contribution of the Center for Molecular Composition Studies of INEOS RAS is gratefully acknowledged.
No human or animal subjects were used in this research.
The authors declare no competing interests.
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, Vol. 72, No. 5, pp. 1268–1273, May, 2023.
Rights and permissions
About this article
Cite this article
Yufryakov, V.S., Tsvetikova, M.A., Bystrova, N.A. et al. Chemo-enzymatic synthesis of (S,S)-2,2′-(ethylenediamino)dibutan-1-ol. Russ Chem Bull 72, 1268–1273 (2023). https://doi.org/10.1007/s11172-023-3900-4
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11172-023-3900-4