TY  - JOUR
AU  - Drašković, Bojana M.
AU  - Bogdanović, Goran A.
AU  - Neelakantan, M. A.
AU  - Chamayou, Anne-Christine
AU  - Thalamuthu, S.
AU  - Avadhut, Yamini S.
AU  - Guenne, Joern Schmedt Auf Der
AU  - Banerjee, Sharmila
AU  - Janiak, Christoph
PY  - 2010
UR  - https://vinar.vin.bg.ac.rs/handle/123456789/3938
AB  - A double zwitterionic Schiff base was synthesized using the amino acid L-histidine and o-vanillin (2-hydroxy-3-methoxy benzaldehyde). Both the phenol and carboxyl groups are deprotonated, and the imine nitrogen atom and histidine-imidazole ring are protonated to give the double zwitterion with an intramolecular (imine)N-H(+)center dot center dot center dot(-)O(phenol) hydrogen bond (ketoamine form). Such a ketoamine form in a double zwitterion is assumed in the catalytic cycle of enzymatic transformations of amino acids with the cofactor (vitamin B6) pyridoxal-5-phosphate (PLP). A high-resolution, low-temperature, single-crystal X-ray diffraction data set on N-o-vanillylidene-l-histidine (also named 3-methoxysalicylidene-l-histidine or N-(2-oxy-3-methoxy-benzylidene)-L-histidine, OVHIS) is used in the analysis of molecular electrostatic properties and intermolecular interactions. All oxygen atoms in the molecule (four in total) are mutually almost coplanar and located (externally) on the same side of molecule. These four O atoms carry significant negative charge and form a large area of strong negative electrostatic potential (appropriate for bonding to a metal atom). The protonated and, thus, positively charged imidazole ring is situated on the opposite side of the molecule from the area of the O atoms. Consequently, the OVHIS molecule is highly polarized and has a very high molecular dipole moment of 42.4 D in the solid state (calculated from experimental X-ray data). Two strong intermolecular charge-assisted N-H(+)center dot center dot center dot(-)O hydrogen bonds (with H center dot center dot center dot O distances of 1.61 angstrom) together with other D-H center dot center dot center dot O interactions (D = N, C) contribute to a large molecular dipole enhancement which occurs upon crystallization. The topologies of the bonding within the molecule as well as its hydrogen bonds have been investigated according to Baders quantum theory of atoms in molecules (QTAIM). (1)H solid-state magic angle spinning nuclear magnetic resonance (MAS NMR) was used to confirm the zwitterionic structure in the solid state.
T2  - Crystal Growth and Design
T1  - N-o-Vanillylidene-L-histidine: Experimental Charge Density Analysis of a Double Zwitterionic Amino Acid Schiff-Base Compound
VL  - 10
IS  - 4
SP  - 1665
EP  - 1676
DO  - 10.1021/cg901239v
ER  - 

@article{
author = "Drašković, Bojana M. and Bogdanović, Goran A. and Neelakantan, M. A. and Chamayou, Anne-Christine and Thalamuthu, S. and Avadhut, Yamini S. and Guenne, Joern Schmedt Auf Der and Banerjee, Sharmila and Janiak, Christoph",
year = "2010",
abstract = "A double zwitterionic Schiff base was synthesized using the amino acid L-histidine and o-vanillin (2-hydroxy-3-methoxy benzaldehyde). Both the phenol and carboxyl groups are deprotonated, and the imine nitrogen atom and histidine-imidazole ring are protonated to give the double zwitterion with an intramolecular (imine)N-H(+)center dot center dot center dot(-)O(phenol) hydrogen bond (ketoamine form). Such a ketoamine form in a double zwitterion is assumed in the catalytic cycle of enzymatic transformations of amino acids with the cofactor (vitamin B6) pyridoxal-5-phosphate (PLP). A high-resolution, low-temperature, single-crystal X-ray diffraction data set on N-o-vanillylidene-l-histidine (also named 3-methoxysalicylidene-l-histidine or N-(2-oxy-3-methoxy-benzylidene)-L-histidine, OVHIS) is used in the analysis of molecular electrostatic properties and intermolecular interactions. All oxygen atoms in the molecule (four in total) are mutually almost coplanar and located (externally) on the same side of molecule. These four O atoms carry significant negative charge and form a large area of strong negative electrostatic potential (appropriate for bonding to a metal atom). The protonated and, thus, positively charged imidazole ring is situated on the opposite side of the molecule from the area of the O atoms. Consequently, the OVHIS molecule is highly polarized and has a very high molecular dipole moment of 42.4 D in the solid state (calculated from experimental X-ray data). Two strong intermolecular charge-assisted N-H(+)center dot center dot center dot(-)O hydrogen bonds (with H center dot center dot center dot O distances of 1.61 angstrom) together with other D-H center dot center dot center dot O interactions (D = N, C) contribute to a large molecular dipole enhancement which occurs upon crystallization. The topologies of the bonding within the molecule as well as its hydrogen bonds have been investigated according to Baders quantum theory of atoms in molecules (QTAIM). (1)H solid-state magic angle spinning nuclear magnetic resonance (MAS NMR) was used to confirm the zwitterionic structure in the solid state.",
journal = "Crystal Growth and Design",
title = "N-o-Vanillylidene-L-histidine: Experimental Charge Density Analysis of a Double Zwitterionic Amino Acid Schiff-Base Compound",
volume = "10",
number = "4",
pages = "1665-1676",
doi = "10.1021/cg901239v"
}

Drašković, B. M., Bogdanović, G. A., Neelakantan, M. A., Chamayou, A., Thalamuthu, S., Avadhut, Y. S., Guenne, J. S. A. D., Banerjee, S.,& Janiak, C.. (2010). N-o-Vanillylidene-L-histidine: Experimental Charge Density Analysis of a Double Zwitterionic Amino Acid Schiff-Base Compound. in Crystal Growth and Design, 10(4), 1665-1676.
https://doi.org/10.1021/cg901239v

Drašković BM, Bogdanović GA, Neelakantan MA, Chamayou A, Thalamuthu S, Avadhut YS, Guenne JSAD, Banerjee S, Janiak C. N-o-Vanillylidene-L-histidine: Experimental Charge Density Analysis of a Double Zwitterionic Amino Acid Schiff-Base Compound. in Crystal Growth and Design. 2010;10(4):1665-1676.
doi:10.1021/cg901239v .

Drašković, Bojana M., Bogdanović, Goran A., Neelakantan, M. A., Chamayou, Anne-Christine, Thalamuthu, S., Avadhut, Yamini S., Guenne, Joern Schmedt Auf Der, Banerjee, Sharmila, Janiak, Christoph, "N-o-Vanillylidene-L-histidine: Experimental Charge Density Analysis of a Double Zwitterionic Amino Acid Schiff-Base Compound" in Crystal Growth and Design, 10, no. 4 (2010):1665-1676,
https://doi.org/10.1021/cg901239v . .