Synthesis of N-quinonyltaurines

S. Gorohovsky; G. Temtsin-Krayz; Shmuel Bittner

doi:10.1007/s00726-002-0407-4

Synthesis of N-quinonyltaurines

S. Gorohovsky, G. Temtsin-Krayz, Shmuel Bittner

Department of Chemistry

Research output: Contribution to journal › Article › peer-review

6 Scopus citations

Abstract

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.

Original language	English
Pages (from-to)	281-287
Number of pages	7
Journal	Amino Acids
Volume	24
Issue number	3
DOIs	https://doi.org/10.1007/s00726-002-0407-4
State	Published - 1 Apr 2003

Keywords

Amino acids
Isocyanates
Isocyanurate
Quinones
Taurine

ASJC Scopus subject areas

Biochemistry
Clinical Biochemistry
Organic Chemistry

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10.1007/s00726-002-0407-4

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abstract = "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.",

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AU - Temtsin-Krayz, G.

AU - Bittner, Shmuel

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N2 - 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.

AB - 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.

KW - Amino acids

KW - Isocyanates

KW - Isocyanurate

KW - Quinones

KW - Taurine

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ER -

Synthesis of N-quinonyltaurines

Abstract

Keywords

ASJC Scopus subject areas

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