Long-lived reactive intermediate photogenerated from N-(5-azido-2-nitrobenzoyl)-N '-(D-biotinyl)-1,2-diaminoethane as an affinity reagent to streptavidin

Long-lived reactive intermediate photogenerated from N-(5-azido-2-nitrobenzoyl)-N '-(D-biotinyl)-1,2-diaminoethane as an affinity reagent to streptavidin Full article

Journal

Journal of Photochemistry and Photobiology B: Biology
ISSN: 1011-1344

Output data

Year: 2001, Volume: 61, Number: 1-2, Pages: 68-77 Pages count : 10 DOI: 10.1016/S1011-1344(01)00147-6

Tags

arylazide; photoaffinity labelling; photobiotin analogues; streptavidin; long-lived intermediate

Authors

Popova Tatyana V. ¹ , Denisov Alexey Yu. ¹ , Shakirov Makhmut M. ² , Komarova Nina I. ¹ , Alekseyev Pavel V. ¹ , Serebriakova Marina V. ³ , Godovikova Tatyana S. ¹

Affiliations

1	Novosibirsk Institute of Bioorganic Chemistry of the Siberian branch of the Russian Academy of Science, 8 Lavrentiev prosp., Novosibirsk 630090, Russia
2	Novosibirsk Institute of Organic Chemistry of the Siberian branch of the Russian Academy of Science, 9 Lavrentiev prosp., Novosibirsk 630090, Russia
3	M.M. Shemyakin–Yu.A. Ovchinnikov Institute of Bioorganic Chemistry of the Russian Academy of Science, Mikluho-Maklaya st. 10/16, Moscow 117871, Russia

Irradiation of a complex between N-(5-azido-2-nitrobenzoyl)-N '-(D-biotinyl)-1,2-diaminoethane (I) and streptavidin with light of 313 nm led to the covalent attachment of the photobiotin analogue I to the protein. Streptavidin could also be labelled in the dark with prephotolyzed I. These results indicate that a long-lived reactive intermediate was formed upon irradiation. Moreover, after cleavage of labelled streptavidin with proteinase K this intermediate appears to be covalently attached to the same peptide as the one obtained by direct photoaffinity labelling. An iminosulfurane II derived from the reaction of biotin sulfur atom with aryl nitrene is responsible for the dark-labelling reaction. The photoproduct II converts in an aqueous solution almost completely into N-(5-amino-2-nitrobenzoyl)-N '-(D-(S-oxo)biotinyl)-1,2-diaminoethane (the half-life of II is 10 days). (C) 2001 Elsevier Science B.V. All rights reserved.

Popova T.V. , Denisov A.Y. , Shakirov M.M. , Komarova N.I. , Alekseyev P.V. , Serebriakova M.V. , Godovikova T.S.
Long-lived reactive intermediate photogenerated from N-(5-azido-2-nitrobenzoyl)-N '-(D-biotinyl)-1,2-diaminoethane as an affinity reagent to streptavidin
Journal of Photochemistry and Photobiology B: Biology. 2001. V.61. N1-2. P.68-77. DOI: 10.1016/S1011-1344(01)00147-6 WOS Scopus OpenAlex

Published print:

Aug 1, 2001

Web of science:	WOS:000170588100009
Scopus:	2-s2.0-0035881930
OpenAlex:	W2044686442

DB	Citing
Web of science	2
Scopus	3
OpenAlex	1