Synthesis of N-quinonyltaurines.
Both 1,4-benzoquinones and 1,4-naphthoquinones were attached to the non-proteinogenic amino acid taurine to form N-quinonyl taurine derivatives. The products were formed via the direct Michael-like addition or by substitution of a good leaving group. An attempt to bridge the two moieties via an ureido spacer resulted in the formation of a bis-quinonylamino isocyanurate derivative. Preliminary MO calculations provided internal ground-state geometries and orbital coefficients of the HOMO levels in two representing taurine conjugates.
Gorohovsky
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Department of Chemistry, Ben-Gurion University of the Negev, Beer-Sheva 84105, Israel.
Temtsin-Krayz
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Bittner
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D016227:Benzoquinones / Q000737:chemistry; D008956:Models, Chemical; D008958:Models, Molecular; D015394:Molecular Structure; D009285:Naphthoquinones / Q000737:chemistry; D011809:Quinones / Q000737:chemistry*; D013654:Taurine / Q000138:chemical synthesis* / Q000737:chemistry
D016227:Benzoquinones; D009285:Naphthoquinones; D011809:Quinones; D013654:Taurine; C035342:1,4-naphthoquinone