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PubMed1993

Synthesis of Benzylglucosinolate in Tropaeolum majus L. (Isothiocyanates as Potent Enzyme Inhibitors).

Benzylglucosinolate accumulates in mature plants of Tropaeolum majus L. The biosynthetic capacity for synthesis of benzylglucosinolate and the total content of benzylglucosinolate have been investigated during plant development and in different tissues. The content increased from 5 mg of benzylglucosinolate in the fresh seed to between 200 and 400 mg in the adult plant, depending on size. The biosynthetic capacity was measured using L-[U-14C]phenylalanine as precursor. Incorporation levels of approximately 30% were obtained with green leaves, whereas the incorporation levels obtained with other tissues were in the range of 0 to 5%. Leaves were the primary site of benzylglucosinolate synthesis. The high amounts of benzylglucosinolate accumulated in other tissues (e.g. developing seeds) reflected transport of benzylglucosinolate from the leaves. The initial steps in the biosynthesis of glucosinolates and cyanogenic glycosides are thought to be similar and to be localized on microsomal membranes. However, a microsomal system prepared from T. majus was biosynthetically inactive. Inclusion of T. majus plant material during preparation of sorghum microsomes also inhibited their activity. Benzylisothiocyanate, generated by degradation of benzylglucosinolate during the homogenization procedure, strongly inhibited the sorghum enzyme system, and its presence may thus explain why the isolated T. majus microsomal system is inactive.

Journal Article↗
PubMed1967

The Biosynthesis of Some Isothiocyanates and Oxazolidinethiones in Rape (Brassica campestris L.).

The incorporation of the radioactivity from acetate-1-(14)C, acetate-2-(14)C, dl-methionine-1-(14)C, dl-methionine-2-(14)C, dl-methionine-3,4-(14)C, dl-homomethionine-2-(14)C, dl-allyl-glycine-2-(14)C, and dl-2-amino-5-hydroxyvalerate-2-(14)C into the aglycones of progoitrin, gluconapin, and glucobrassicanapin of maturing rape plants (Brassica campestris L.) was investigated. Radioactivity from dl-methionine-2-(14)C, dl-methionine-3,4-(14)C, dl-homomethionine-2-(14)C, and acetate-2-(14)C were incorporated into the 3 major thioglucosides. The other organic compounds were poorly incorporated except for dl-allylglycine-2-(14)C into glucobrassicanapin. The results obtained suggest that the rape plant can synthesize amino acids by the condensation of acetate (as acetyl CoA) to alpha-keto acids to yield a homologue of the original amino acid. These newly formed amino acids are then employed to synthesize the 3 major thioglucosides.

Journal Article↗
PubMed2003

The isothiocyanate complex of triphenylborane forms an unusual coordination polymer with [K(18-crown-6)](+), both in the solid state and in solution.

The title salt, (1,4,7,10,13,16-hexaoxacyclooctadecane-kappa(6)O)[(isothiocyanato)triphenylborato-kappaS]potassium(I), [K(C(19)H(15)BNS)(C(12)H(24)O(6))] or [K(SCNBPh(3))(18-crown-6)], where 18-crown-6 is 1,4,7,10,13,16-hexaoxacyclooctadecane and [SCNBPh(3)](-) is the (isothiocyanato)triphenylborate anion, exhibits a supramolecular structure that is best described as a helical coordination polymer or molecular screw. This unusual supramolecular structure is based on a framework in which the SCN(-) ion bridges the chelated K(+) ion and the B atom of BPh(3) in a micro(2) fashion. The X-ray crystal structure of the title salt has been determined at 100 (1) and 293 (2) K. The K(+) ion exhibits axial ligation by the S atom of the [SCNBPh(3)](-) anion, with a K-S distance of 3.2617 (17) A (100 K). The trans-axial ligand is an unexpected eta(2)-bound C=C bond of a phenyl group (meta- and para-C atoms) that belongs to the BPh(3) moiety of a neighboring molecule. The K-C bond distances span the range 3.099 (3)-3.310 (3) A (100 K) and are apparently retained in CDCl(3) solution (as evidenced by (13)C NMR spectroscopy). By virtue of the latter interaction, the supramolecular structure is a helical coordination polymer, with the helix axis parallel to the b axis of the unit cell. IR spectroscopy and semi-empirical molecular orbital (AM1) calculations have been used to investigate further the electronic structure of the [SCNBPh(3)](-) ion.

Journal Article↗
PubMed2004

Two furopyridine complexes of nickel(II) isothiocyanate.

Pyridine fused with a furan ring (fupy), and its dimethyl derivative, have been used for the first time as ligands to synthesize potentially new Werner clathrates. The extended aromatic system of pyridine-like ligands influences considerably the molecular structure of prepared nickel complexes. The molecular structure of tetrakis(furo[3,2-c]pyridine)bis(isothiocyanato)nickel(II) tetrahydrofuran (THF) solvate, [Ni(NCS)(2)(C(7)H(5)NO)(4)].C(4)H(8)O or [Ni(NCS)(2)(fupy)(4)].THF, (I), reveals a 'four-blade propeller' arrangement of ligands, with the angles between the fupy planes and the basal octahedron plane spanning the range 38.7-55.3 degrees. These angles are much larger (69.9-78.8 degrees ) in the centrosymmetric complex tetrakis(2,3-dimethylfuro[3,2-c]pyridine)bis(isothiocyanato)nickel(II) 6.6-hydrate, [Ni(NCS)(2)(C(9)H(9)NO)(4)].6.6H(2)O or [Ni(NCS)(2)(Me(2)fupy)(4)].6.6H(2)O, (II), in which crystallographically imposed inversion symmetry is present.

Journal Article↗
PubMed1975

An approach to quantitation in rhodamine isothiocyanate labeling.

A survey of commercially available TMRI and RBI products revealed that many are of unsatisfactory quality. Optimum dye/IgG ratios were obtained in conjugates with TMRI of about 65% purity by labeling them with reaction mixture ratios of 10 and 20 mug dye/mg IgG. Optimum labeling with RBI of comparable purity required reaction mixture ratios of at least 20 mug dye/mg IgG. Although specific storage stability studies of TMRI or RBI products were not performed, one TMRI product underwent appreciable degradation during a 2-year period of storage in a desiccator over Drierite. The importance of evaluating the protein labeling capacity of TMRI or RBI products before making immune conjugate preparations is evident.

Animals↗
PubMed1976

Abnormal behaviour of proline in the isothiocyanate degradation.

It has been observed that proline residues often initiate overlaps during sequenator analysis. The cause has been shown to be an abnormally slow cleavage reaction. The kinetics of the cleavage reaction has been studied and found to obey pseudo-first-order kinetics. There are considerable differences in reaction rates depending on the position of proline in the sequence, as demonstrated for the four prolines in the N-terminal section of the H2B histone from chicken.

Amino Acid Sequence↗