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Paper | Regular issue | Vol 65, No. 12, 2005, pp.2917-2924
Published online, 7th October, 2005
DOI: 10.3987/COM-05-10544
Stereochemistry of Fully Acetylated Tetrahydropterins and Tetrahydroquinoxalines

Ning Chen, Kazuhisa Ikemoto, Shingo Komatsu, and Shizuaki Murata*

*Graduate School of Environmental Studies, Nagoya University, Chikusa, Nagoya, 464-8601, Japan

Abstract

Completely acetylated derivatives of naturally occurring tetrahydro-D-monapterin, (6R)-2-acetamido-6-[(1R,2R)-1,2,3-triacetoxypropyl]-5,8-diacetyl-5,6,7,8-tetrahydropteridin-4(3H)-one, show plus and minus CD signs at λ 280 and 240 nm, respectively. Similar CD spectra are obtained on (2S)-1,4-diacetyl-1,2,3,4-tetrahydro-2-isopropylquinoxaline and (2S)-1,4-diacetyl-1,2,3,4-tetrahydro-2-isobutylquinoxaline but not on (2S)-1,4-diacetyl-1,2,3,4-tetrahydro-2-methylquinoxaline nor on the 2-ethyl derivative. The similarity of their CD spectra is represented the same stereogenic structure based on the boat conformation confirmed by X-Ray crystallographic analyses.