A. Ray, Zhenjia Chen, R. Stark
Sep 3, 1998
Citations
2
Influential Citations
27
Citations
Journal
Phytochemistry
Abstract
Abstract The chemical deprotecting reagent iodotrimethylsilane has been used to achieve controlled breakdown of ester bonds in cutin, an insoluble protective biopolymer obtained from the fruit of Citrus aurantifolia (limes). Four soluble products that preserve essential features of the cuticular molecular architecture have been isolated chromatographically and identified by multidimensional NMR and liquid secondary-ion mass spectrometry, whereas the insoluble residue has been characterized by solid state 13 C NMR spectroscopy. The building blocks of the two dimers and one tetramer include the major Citrus cutin monomers 16-hydroxy-10-oxo-hexadecanoic acid and 10,16-dihydroxyhexadecanoic acid, which are joined by primary ester linkages. The CPMAS 13 C NMR spectra of the unreacted residue implicate a heterogeneous reaction in which esters of primary alcohols within the cross-linked cutin network are preferentially cleaved. These studies offer a direct and definitive description of molecular connectivities within the protective polyesters of fruit cuticles.