IAN (indole-3-acetonitrile) is a candidate IAA precursor in the tryptophan-independent pathway of auxin biosynthesis (dashed line of figure above) (Normanly et al, 1993). IAN accumulates 6- to 11-fold in the Arabidopsis trp3 and trp2 mutants that overaccumulate IAA conjugates (trp3 mutants are defective in tryptophan synthase [EC 4.2.1.20] A subunit; trp2 mutants are defective in tryptophan synthase B subunit) (Bartel, 1997). Genes encoding nitrilase [EC 3.5.5.1] enzymes have been cloned from Arabidopsis and several other higher plants (Bartling et al, 1994; Normanly et al, 1997).

IAN has several auxin-like effects in Arabidopsis, and is metabolized to IAA. An Arabidopsis mutant defective in the nitrilase encoded by the NIT1 gene has been identified, but the half-life of IAN and the levels of IAA and IAN were unaffected in the nit1 mutant. This may be because Arabidopsis has other functional nitrilases (e.g. 3 nitrilase genes, NIT1, NIT2 and NIT3 are clustered on chromosome 3). However, overexpression of NIT2 enhanced IAN turnover and increased sensitivity to IAN (Normanly et al, 1997).

Bartel B 1997 Auxin biosynthesis. Annu. Rev. Plant Physiol. Plant Mol. Biol. 48: 51-66.

Bartling D, Seedorf M, Schmidt RC, Weiler EW 1994 Molecular characterization of two cloned nitrilases from Arabidopsis thaliana: key enzymes in biosynthesis of the plant hormone indole-3-acetic acid. PNAS 91: 6021-6025.

Normanly J, Cohen JD, Fink GR 1993 Arabidopsis thaliana auxotrophs reveal a tryptophan-independent biosynthetic pathway for indole-3-acetic acid. Proc. Natl. Acad. Sci. U.S.A. 90: 10355-10359.

Normanly J, Grisafi P, Fink GR, Bartel B 1997 Arabidopsis mutants resistant to the auxin effects of indole-3-acetonitrile are defective in the nitrilase encoded by the NIT1 gene. Plant Cell 9: 1781-1790.