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Synthesis of biopterin and related pterin glycosides
Author(s) -
Hanaya Tadashi,
Yamamoto Hiroshi
Publication year - 2013
Publication title -
iubmb life
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.132
H-Index - 113
eISSN - 1521-6551
pISSN - 1521-6543
DOI - 10.1002/iub.1137
Subject(s) - pterin , biopterin , glycosidic bond , chemistry , glycoside , glycosyl , biochemistry , stereochemistry , enzyme , cofactor , tetrahydrobiopterin
Certain pterins having a hydroxyalkyl side chain at C‐6 have been found as glycosidic forms in certain prokaryotes, such as 2′‐ O ‐(α‐ D ‐glucopyranosyl)biopterin from various kinds of cyanobacteria, and limipterin from a green sulfur photosynthetic bacterium. Synthetic studies on glycosides of biopterin and related pterins have been made in view of the structural proof as well as for closer examination of their biological activities and functions. The syntheses of these natural pterin glycosides have effectively been achieved, mostly through appropriately protected N 2 ‐( N , N ‐dimethylaminomethylene)‐3‐[2‐(4‐nitrophenyl)ethyl]pterin derivatives as glycosyl acceptors, and are reviewed here. © 2013 IUBMB Life 65(4):300–309, 2013.