Stereochemistry of fully acetylated tetrahydropterins and tetrahydroquinoxalines

Ning Chen, Kazuhisa Ikemoto, Shingo Komatsu, Shizuaki Murata

Research output: Contribution to journalArticlepeer-review

4 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)2917-2924
Number of pages8
JournalHeterocycles
Volume65
Issue number12
DOIs
Publication statusPublished - 01-12-2005

All Science Journal Classification (ASJC) codes

  • Analytical Chemistry
  • Pharmacology
  • Organic Chemistry

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