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
✍ Scribed by Ki W. Cha; Wolfgang Pfleiderer; Jeongbin J. Yim
- Publisher
- John Wiley and Sons
- Year
- 1995
- Tongue
- German
- Weight
- 677 KB
- Volume
- 78
- Category
- Article
- ISSN
- 0018-019X
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✦ Synopsis
A new pteridine compound was isolated from green sulfur photosynthetic bacteria, Chlorobiurn limicolu f . ihiostiifurn~~hilum NCIB 8327. The structure of this pterin derivative was established to be 1-U-(~-erythro-S,6,7,8tetrahydropterin-2'-yl)-P-N-acetylglucosamine (1) from 'H-NMR and CD spectra as well as from various massspectrometric 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. Electi-ospray (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, 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.