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Volume 10
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10.3390/cryst10121133
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Article

“Free of Base” Sulfa-Michael Addition for Novel o-Carboranyl-DL-Cysteine Synthesis †

by
Julia Laskova
1,*,
Irina Kosenko
1,
Ivan Ananyev
1,
Marina Stogniy
1,2,
Igor Sivaev
1 and
Vladimir Bregadze
1
1
A.N.Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, Vavilova str. 28, 119991 Moscow, Russia
2
M.V. Lomonosov Institute of Fine Chemical Technology, MIREA—Russian Technological University, 86 Vernadsky Av., 119571 Moscow, Russia
*
Author to whom correspondence should be addressed.
†
Dedicated to Professor Alan J. Welch in recognition of his outstanding contribution in the chemistry of carboranes.
Crystals 2020, 10(12), 1133; https://doi.org/10.3390/cryst10121133
Submission received: 2 November 2020 / Revised: 1 December 2020 / Accepted: 7 December 2020 / Published: 11 December 2020
(This article belongs to the Special Issue Carborane: Dedicated to the Work of Professor Alan Welch)
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Abstract

The sulfa-Michael addition reaction was applied for the two-step synthesis of o-carboranyl cysteine 1-HOOCCH(NH2)CH2S-1,2-C2B10H11 from the trimethylammonium salt of 1-mercapto-o-carborane and methyl 2-acetamidoacrylate. To avoid the decapitation of o-carborane into its nido-form, the “free of base” method under mild conditions in a system of two immiscible solvents toluene-H2O was developed. The replacement of H2O by 2H2O resulted in carboranyl-cysteine containing a deuterium label at the α-position of the amino acid 1-HOOCCD(NH2)CH2S-1,2-C2B10H11. The structure of the protected o-carboranyl cysteine was determined by single-crystal X-ray diffraction. The obtained compounds can be considered as potential agents for the Boron Neutron Capture Therapy of cancer.
Keywords: boron chemistry; o-carborane; sulfa-Michael addition reaction; cysteine; boron neutron capture therapy; o-carborane decapitation; labeled compound boron chemistry; o-carborane; sulfa-Michael addition reaction; cysteine; boron neutron capture therapy; o-carborane decapitation; labeled compound

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MDPI and ACS Style

Laskova, J.; Kosenko, I.; Ananyev, I.; Stogniy, M.; Sivaev, I.; Bregadze, V. “Free of Base” Sulfa-Michael Addition for Novel o-Carboranyl-DL-Cysteine Synthesis. Crystals 2020, 10, 1133. https://doi.org/10.3390/cryst10121133

AMA Style

Laskova J, Kosenko I, Ananyev I, Stogniy M, Sivaev I, Bregadze V. “Free of Base” Sulfa-Michael Addition for Novel o-Carboranyl-DL-Cysteine Synthesis. Crystals. 2020; 10(12):1133. https://doi.org/10.3390/cryst10121133

Chicago/Turabian Style

Laskova, Julia, Irina Kosenko, Ivan Ananyev, Marina Stogniy, Igor Sivaev, and Vladimir Bregadze. 2020. "“Free of Base” Sulfa-Michael Addition for Novel o-Carboranyl-DL-Cysteine Synthesis" Crystals 10, no. 12: 1133. https://doi.org/10.3390/cryst10121133

APA Style

Laskova, J., Kosenko, I., Ananyev, I., Stogniy, M., Sivaev, I., & Bregadze, V. (2020). “Free of Base” Sulfa-Michael Addition for Novel o-Carboranyl-DL-Cysteine Synthesis. Crystals, 10(12), 1133. https://doi.org/10.3390/cryst10121133

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