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1,3-dipolar cycloaddition in the synthesis of glycoconjugates of natural chlorins and bacteriochlorins Научная публикация

Журнал Journal of Porphyrins and Phthalocyanines
ISSN: 1099-1409 , E-ISSN: 1088-4246
Вых. Данные Год: 2009, Том: 13, Номер: 03, Страницы: 336-345 Страниц : 10 DOI: 10.1142/s1088424609000425
Авторы Grin Mikhail A. 1 , Lonin Ivan S. 1 , Lakhina Anna A. 1 , Ol'shanskaya Elena S. 1 , Makarov Alexey I. 1 , Sebyakin Yury L. 1 , Guryeva Lyudmila Yu. 1 , Toukach Philip V. 2 , Kononikhin Alexey S. 3 , Kuzmin Vladimir A. 3 , Mironov Andrey F. 1
Организации
1 M.V. Lomonosov Moscow Academy of Fine Chemical Technology, Moscow, Russian Federation
2 N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russian Federation
3 Emanuel Institute of Biochemical Physics, Russian Academy of Sciences, Moscow, Russian Federation

Реферат: Glucose-, galactose- and lactose-containing photosensitizers based on derivatives of chlorophyll a and bacteriochlorophyll a were synthesized with the use of [3+2] cycloaddition between sugar azides and triple bond derivatives of chlorins and bacteriochlorins. Unlike bacteriochlorin cycloimide, chlorin was detected to form a Cu-complex during the click reaction. An approach to the synthesis of metal-free glycosylated chlorins was developed with the use of "protection" by Zn2+ cation and subsequent demetalation. It is based on the action of alkynyl chlorin e6 derivative Zn-complex, which is resistant to the substitution by copper cation. Bacteriochlorin p cycloimide conjugate with per-acetylated β-D-lactose was obtained and shown to become water-soluble after unblocking of the lactose hydroxy functions. NMR studies allowed for the elucidation of structure, tautomeric form and conformation of the obtained compounds.
Библиографическая ссылка: Grin M.A. , Lonin I.S. , Lakhina A.A. , Ol'shanskaya E.S. , Makarov A.I. , Sebyakin Y.L. , Guryeva L.Y. , Toukach P.V. , Kononikhin A.S. , Kuzmin V.A. , Mironov A.F.
1,3-dipolar cycloaddition in the synthesis of glycoconjugates of natural chlorins and bacteriochlorins
Journal of Porphyrins and Phthalocyanines. 2009. V.13. N03. P.336-345. DOI: 10.1142/s1088424609000425 WOS Scopus OpenAlex
Идентификаторы БД:
≡ Web of science: WOS:000266134500006
≡ Scopus: 2-s2.0-78649894946
≡ OpenAlex: W1988180070
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