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Quantum chemical conformational analysis of the auxin phytohormone 4-methyl-3-indole acetic acid (CROSBI ID 86676)

Prilog u časopisu | izvorni znanstveni rad | međunarodna recenzija

Ramek, Michael ; Tomić, Sanja Quantum chemical conformational analysis of the auxin phytohormone 4-methyl-3-indole acetic acid // International journal of quantum chemistry, 75 (1999), 6; 1003-1008-x

Podaci o odgovornosti

Ramek, Michael ; Tomić, Sanja

engleski

Quantum chemical conformational analysis of the auxin phytohormone 4-methyl-3-indole acetic acid

The potential energy surface of 4-methyl-indole-3-acetic acid (4-Me-IAA) contains five symmetry unique minima. Similar to 4-Et-IAA, the global minimum is not mirror-symmetrical but has a tilted acetic acid side chain. The carbonyl oxygen atom comes close enough to one of the methyl group hydrogen atoms (distance: 2.575 Å) to form a weak hydrogen bond (bond order: 0.018), which is weaker than the corresponding H-bond in the global minimum of 4-Et-IAA. The mirror symmetrical local minimum contains a different C-H···O=C hydrogen bond of similar strength (distance: 2.329 Å, bond order: 0.018), but also two repulsive H···H interactions between the methyl and the acetic acid side chain (distances: 2.405 Å). The reaction paths of 4-Me-IAA show characteristic elements of both, IAA and 4-Cl-IAA. In a qualitative sense, 4-Me-IAA thus is inbetween IAA and 4-Cl-IAA, which has a fascinating equivalence in the biological activity data: Rescher et al. studied the correlation between binding affinity and maximum growth rate of meize coleoptil section at the optimum concentration of 10 mol/l for several compounds and determined the following order: naphthalene-1-acetic acid > 4-Cl-IAA > 4-Me-IAA > IAA > 4-Et-IAA > 2-Me-IAA. In this order, 4-Me-IAA also takes a position between IAA and 4-Cl-IAA, although this could be explained in part by the higher lipophilicity of the chlorinated compounds.

Auxin; ab initio calculation; conformational analysis; 4-Me-indole-3-acetic acid

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Podaci o izdanju

75 (6)

1999.

1003-1008-x

objavljeno

0020-7608

Povezanost rada

Kemija

Indeksiranost