Mixed cobalt(III) complexes with aromatic amino acids and diamine. Part II. Synthesis and configuration of (1,2-diaminoethane)Bis(L-Tyrosinato)-cobalt(III)complex diastereomers. The crystal structure of the Δ-C                         1                         -Cis(O) diastereomer

Dj U. Miodragović; G. A. Bogdanović; S. M. Milosavljević; M. J. Malinar; M. B. Ćeleap; A. Spasojević-de Biré; S. Macura; N. Juranić

Mixed cobalt(III) complexes with aromatic amino acids and diamine. Part II. Synthesis and configuration of (1,2-diaminoethane)Bis(L-Tyrosinato)-cobalt(III)complex diastereomers. The crystal structure of the Δ-C ₁ -Cis(O) diastereomer

Dj U. Miodragović, G. A. Bogdanović, S. M. Milosavljević, M. J. Malinar, M. B. Ćeleap, A. Spasojević-de Biré, S. Macura, N. Juranić

Biochemistry and Molecular Biology

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

7 Scopus citations

Abstract

In the reaction of trans-[CoCl ₂ (en) ₂ ] ⁺ with L-tyrosine all six theoretically possible diastereomers of the (1,2-diaminoethane)bis(L-tyrosinato) cobalt(III) complex were formed. The following five were isolated: Λ-trans(O); and Λ- and Δ-C ₂ -cis(O) and Λ- and Δ-C ₁ -cis(O) diastereomers, while the Δ-trans(O) diastereomer was only detected in the corresponding eluate. Separation of the obtained diastereomers was performed by chromatography on a Dowex 1 x 4 column. Characterization of the isolated diastereomers was carried out by means of elemental analysis, electronic absorption, circular dichroic, ¹ H and ¹³ CNMR spectra, and by x-ray crystal structure analysis in the case of the Δ-C ₁ -cis(O) diastereomer. We established the general rule of preference of diasteromers formation in complexes of [Co(L-aa) ₂ diamine] ⁺ (L-aa=L-amino acid anion; diamine=1,2-diaminoethane or 1,3-diaminopropane) type.

Original language	English (US)
Pages (from-to)	299-308
Number of pages	10
Journal	Enantiomer
Volume	6
Issue number	5
State	Published - 2001

Keywords

CD
Cobalt(III) complex
Crystal structure
L-tyrosine
NMR
Synthesis

ASJC Scopus subject areas

General Chemistry
Biochemistry
General Biochemistry, Genetics and Molecular Biology
Organic Chemistry

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Miodragović, D. U., Bogdanović, G. A., Milosavljević, S. M., Malinar, M. J., Ćeleap, M. B., Spasojević-de Biré, A., Macura, S., & Juranić, N. (2001). Mixed cobalt(III) complexes with aromatic amino acids and diamine. Part II. Synthesis and configuration of (1,2-diaminoethane)Bis(L-Tyrosinato)-cobalt(III)complex diastereomers. The crystal structure of the Δ-C ₁ -Cis(O) diastereomer Enantiomer, 6(5), 299-308.

Mixed cobalt(III) complexes with aromatic amino acids and diamine. Part II. Synthesis and configuration of (1,2-diaminoethane)Bis(L-Tyrosinato)-cobalt(III)complex diastereomers. The crystal structure of the Δ-C ₁ -Cis(O) diastereomer . / Miodragović, Dj U.; Bogdanović, G. A.; Milosavljević, S. M. et al.
In: Enantiomer, Vol. 6, No. 5, 2001, p. 299-308.

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

Miodragović, DU, Bogdanović, GA, Milosavljević, SM, Malinar, MJ, Ćeleap, MB, Spasojević-de Biré, A, Macura, S & Juranić, N 2001, ' Mixed cobalt(III) complexes with aromatic amino acids and diamine. Part II. Synthesis and configuration of (1,2-diaminoethane)Bis(L-Tyrosinato)-cobalt(III)complex diastereomers. The crystal structure of the Δ-C ₁ -Cis(O) diastereomer ', Enantiomer, vol. 6, no. 5, pp. 299-308.

Miodragović DU, Bogdanović GA, Milosavljević SM, Malinar MJ, Ćeleap MB, Spasojević-de Biré A et al. Mixed cobalt(III) complexes with aromatic amino acids and diamine. Part II. Synthesis and configuration of (1,2-diaminoethane)Bis(L-Tyrosinato)-cobalt(III)complex diastereomers. The crystal structure of the Δ-C ₁ -Cis(O) diastereomer Enantiomer. 2001;6(5):299-308.

Miodragović, Dj U. ; Bogdanović, G. A. ; Milosavljević, S. M. et al. / Mixed cobalt(III) complexes with aromatic amino acids and diamine. Part II. Synthesis and configuration of (1,2-diaminoethane)Bis(L-Tyrosinato)-cobalt(III)complex diastereomers. The crystal structure of the Δ-C ₁ -Cis(O) diastereomer In: Enantiomer. 2001 ; Vol. 6, No. 5. pp. 299-308.

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title = " Mixed cobalt(III) complexes with aromatic amino acids and diamine. Part II. Synthesis and configuration of (1,2-diaminoethane)Bis(L-Tyrosinato)-cobalt(III)complex diastereomers. The crystal structure of the Δ-C 1 -Cis(O) diastereomer ",

abstract = " In the reaction of trans-[CoCl 2 (en) 2 ] + with L-tyrosine all six theoretically possible diastereomers of the (1,2-diaminoethane)bis(L-tyrosinato) cobalt(III) complex were formed. The following five were isolated: Λ-trans(O); and Λ- and Δ-C 2 -cis(O) and Λ- and Δ-C 1 -cis(O) diastereomers, while the Δ-trans(O) diastereomer was only detected in the corresponding eluate. Separation of the obtained diastereomers was performed by chromatography on a Dowex 1 x 4 column. Characterization of the isolated diastereomers was carried out by means of elemental analysis, electronic absorption, circular dichroic, 1 H and 13 CNMR spectra, and by x-ray crystal structure analysis in the case of the Δ-C 1 -cis(O) diastereomer. We established the general rule of preference of diasteromers formation in complexes of [Co(L-aa) 2 diamine] + (L-aa=L-amino acid anion; diamine=1,2-diaminoethane or 1,3-diaminopropane) type. ",

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T1 - Mixed cobalt(III) complexes with aromatic amino acids and diamine. Part II. Synthesis and configuration of (1,2-diaminoethane)Bis(L-Tyrosinato)-cobalt(III)complex diastereomers. The crystal structure of the Δ-C 1 -Cis(O) diastereomer

AU - Miodragović, Dj U.

AU - Bogdanović, G. A.

AU - Milosavljević, S. M.

AU - Malinar, M. J.

AU - Ćeleap, M. B.

AU - Spasojević-de Biré, A.

AU - Macura, S.

AU - Juranić, N.

PY - 2001

Y1 - 2001

N2 - In the reaction of trans-[CoCl 2 (en) 2 ] + with L-tyrosine all six theoretically possible diastereomers of the (1,2-diaminoethane)bis(L-tyrosinato) cobalt(III) complex were formed. The following five were isolated: Λ-trans(O); and Λ- and Δ-C 2 -cis(O) and Λ- and Δ-C 1 -cis(O) diastereomers, while the Δ-trans(O) diastereomer was only detected in the corresponding eluate. Separation of the obtained diastereomers was performed by chromatography on a Dowex 1 x 4 column. Characterization of the isolated diastereomers was carried out by means of elemental analysis, electronic absorption, circular dichroic, 1 H and 13 CNMR spectra, and by x-ray crystal structure analysis in the case of the Δ-C 1 -cis(O) diastereomer. We established the general rule of preference of diasteromers formation in complexes of [Co(L-aa) 2 diamine] + (L-aa=L-amino acid anion; diamine=1,2-diaminoethane or 1,3-diaminopropane) type.

AB - In the reaction of trans-[CoCl 2 (en) 2 ] + with L-tyrosine all six theoretically possible diastereomers of the (1,2-diaminoethane)bis(L-tyrosinato) cobalt(III) complex were formed. The following five were isolated: Λ-trans(O); and Λ- and Δ-C 2 -cis(O) and Λ- and Δ-C 1 -cis(O) diastereomers, while the Δ-trans(O) diastereomer was only detected in the corresponding eluate. Separation of the obtained diastereomers was performed by chromatography on a Dowex 1 x 4 column. Characterization of the isolated diastereomers was carried out by means of elemental analysis, electronic absorption, circular dichroic, 1 H and 13 CNMR spectra, and by x-ray crystal structure analysis in the case of the Δ-C 1 -cis(O) diastereomer. We established the general rule of preference of diasteromers formation in complexes of [Co(L-aa) 2 diamine] + (L-aa=L-amino acid anion; diamine=1,2-diaminoethane or 1,3-diaminopropane) type.

KW - CD

KW - Cobalt(III) complex

KW - Crystal structure

KW - L-tyrosine

KW - NMR

KW - Synthesis

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