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Pteridines. Part CVI . Isolation and characterization of limipterin (1‐ O ‐( L ‐ erythro ‐biopterin‐2′‐yl)‐β‐ N ‐acetylglucosamine) and its 5,6,7,8‐tetrahydro derivative from green sulfur bacterium Chlorobium limicola f. thiosulfatophilum NCIB 8327
Author(s) -
Cha Ki W.,
Pfleiderer Wolfgang,
Yim Jeongbin J.
Publication year - 1995
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.19950780307
Subject(s) - chemistry , pterin , hydrolysis , stereochemistry , diastereomer , pteridine , fast atom bombardment , nuclear magnetic resonance spectroscopy , carbon 13 nmr , n acetylglucosamine , mass spectrometry , organic chemistry , chromatography , enzyme , cofactor
A new pteridine compound was isolated from green sulfur photosynthetic bacteria, Chlorobium limicola f. thiosulfatophilum NCIB 8327. The structure of this pterin derivative was established to be 1‐ O ‐( L ‐ erythro ‐5,6,7,8‐ tetrahydropterin‐2′‐yl)‐β‐ N ‐acetylglucosamine ( 1 ) from 1 H‐NMR and CD spectra as well as from various mass spectrometric techniques and chemical‐cleavage techniques. Upon acid hydrolysis of 1 , equimolar amounts of biopterin ( 2 ) and N ‐acetylglucosamine were produced. The structure of the hydrolysis product 2 was confirmed by comparing its NMR, UV, CD, and MS and its chromatographical behavior with those of an authentic specimen. N ‐Acetylglucosamine was identified by an enzymatic hydrolysis experiment as well as by NMR and thin layer chromatography. Electrospray (ES), fast‐atom‐bombardment (FAB), and thermospray (TS) mass spectrometry of 1 yielded an M H + at m/z 441. Periodate‐oxidation experiments of the intact molecule 1 and of its hydrolysis product 2 are consistent with the proposed structure. Differential I 2 oxidation experiments with the native compound showed that the in vivo oxidation state of this pterin is its tetrahydro form. We propose the trivial name ‘limipterin’ for this new compound.