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Pteridines. Part C . Structure and nonenzymatic synthesis of aurodrosopterin
Author(s) -
Yim Jeongbin,
Kim Sujeong,
Walcher Gunter,
Pfleiderer Wolfgang
Publication year - 1993
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19930760516
Subject(s) - chemistry , pigment , thin layer chromatography , absorption spectroscopy , absorption (acoustics) , stereochemistry , cellulose , chromatography , organic chemistry , physics , quantum mechanics , acoustics
The nonenzymatic synthesis of aurodrosopterin ( 5 ) from 6‐acetyl‐2‐amino‐3, 7, 8, 9‐tetrahydro‐4 H ‐pyrimido‐[4,5‐ b ][1,4]diazepin‐4‐one ( 3 ) and 7,8‐dihydrolumazine ( 4 ) at pH 3 (HCl) was performed. The identity of the synthesized compound with the natural eye pigment isolated from drosophila heads was confirmed by thin‐layer chromatography on cellulose and by comparisons of the 1 H‐NMR and UV/VIS spectra. The nonenzymatic synthesis of a neodrosopterin‐like red pigment from 3 and 2,4‐diamino‐7,8‐dihydropteridine was also carried out, but its identity could not be established. This pigment, called aminodrosopterin, has an absorption peak at 489 nm, which is very close to that of neodrosopterin.