Citation: YANG Le-Le, LIU Jia, LI Yue, LIU Kun, RUAN Wen-Juan. Molecular Recognition of Glycoconjugated Porphyrin with Chiral Amino Acid Methyl Ester[J]. Acta Physico-Chimica Sinica, ;2013, 29(09): 1877-1885. doi: 10.3866/PKU.WHXB201306143 shu

Molecular Recognition of Glycoconjugated Porphyrin with Chiral Amino Acid Methyl Ester

1.
Department of Chemistry, Nankai University, Tianjin 300071, P. R. China

Received Date: 19 April 2013
Available Online: 14 June 2013
Fund Project: 国家自然科学基金(20671053)资助项目 (20671053)

Three atropisomeric tetrasaccharide-substituted zinc porphyrins (αβαβ-Zn-A, ααββ-Zn-A and αααβ-Zn-A) and one monosaccharide-substituted zinc porphyrin (Zn-B) were synthesized. We explored the interactions of these zinc porphyrins with a set of amino acid methyl esters (L/D-LeuOMe, L/ D-ThrOMe, L/D-ValOMe, and L/D-PheOMe)using visible titration and circular dichroism (CD) spectroscopy. We observed that all of them bind to L-amino acid methyl esters more closely than to those with D-configuration. In particular, ααββ-Zn-A gives a high enantioselectivity, K_L/K_D of 4.75, and could be used for chiral recognition of amino acid methyl esters. The binding constants of the three Zn-A compounds with methyl amino acid methyl esters are in the same order, i.e., K^θ(LeuOMe) > K^θ(ValOMe) > K^θ(ThrOMe) > K^θ(PheOMe), but the order of the binding constants for K^θ(PheOMe) > K^θ(LeuOMe) > K^θ(ValOMe) > K^θ(ThrOMe). In addition, we used imidazole as a probe to study the effects of achiral molecules on the conformations of the glycoconjugated porphyrins. The experimental results show that binding with imidazole causes adjustments in the conformations of the Zn-A compounds. The binding constants of the Zn-A compounds with imidazole and with methyl amino acid methyl esters are in the same order: K^θ(ααββ-Zn-A) > K^θ(αβαβ-Zn-A) > K^θ(αααβ-Zn-A).
- Glycoconjugated porphyrin,
- Chiral recognition,
- Spectrum titration,
- Circular dichroism spectroscopy,
- Amino acid methyl ester
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