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

1,3-dipolar cycloaddition in the synthesis of glycoconjugates of natural chlorins and bacteriochlorins Full article

Journal

Journal of Porphyrins and Phthalocyanines
ISSN: 1099-1409 , E-ISSN: 1088-4246

Output data

Year: 2009, Volume: 13, Number: 03, Pages: 336-345 Pages count : 10 DOI: 10.1142/s1088424609000425

Authors

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

Affiliations

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

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.

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

≡ Web of science:	WOS:000266134500006
≡ Scopus:	2-s2.0-78649894946
≡ OpenAlex:	W1988180070