Synthesis of β-keto and α,β-unsaturated N-acetylcysteamine thioesters

Gilbert, Ian H.; Ginty, Mark; O'Neill, John A.; Simpson, Thomas J.; Staunton, James; Willis, Christine L.

doi:10.1016/0960-894x(95)00276-y

Cited by 45 publications

(29 citation statements)

References 11 publications

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“…p-Coumaroyl-CoA (6), cinnamoyl-CoA (10), and feruloyl-CoA (5) were synthesized according to the procedures reported by Blecher [9]. Cinnamoyldiketide-N-acetylcysteamine (NAC), cinnamoyl-p-coumaroylmethane (12), dicinnamoylmethane (11), and cinnamoylferuloylmethane (9) were synthesized according to the previously reported method [10,11].…”

Section: Methodsmentioning

confidence: 99%

Identification and characterization of multiple curcumin synthases from the herb Curcuma longa

Katsuyama

Kita²,

Horinouchi

2009

FEBS Letters

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Edited by Ulf-Ingo Flügge Keywords:Polyketide synthase Curcumin Demethoxycurcumin Bisdemethoxycurcumin Curcuma longa a b s t r a c t Curcuminoids are pharmaceutically important compounds isolated from the herb Curcuma longa. Two additional type III polyketide synthases, named CURS2 and CURS3, that are capable of curcuminoid synthesis were identified and characterized. In vitro analysis revealed that CURS2 preferred feruloyl-CoA as a starter substrate and CURS3 preferred both feruloyl-CoA and p-coumaroyl-CoA. These results suggested that CURS2 synthesizes curcumin or demethoxycurcumin and CURS3 synthesizes curcumin, bisdemethoxycurcumin and demethoxycurcumin. The availability of the substrates and the expression levels of the three different enzymes capable of curcuminoid synthesis with different substrate specificities might influence the composition of curcuminoids in the turmeric and in different cultivars.

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Section: Methodsmentioning

confidence: 99%

Identification and characterization of multiple curcumin synthases from the herb Curcuma longa

Katsuyama

Kita²,

Horinouchi

2009

FEBS Letters

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“…The solvents were removed in vacuo. The products were purified by chromatography using a silica gel column impregnated with anhydrous copper sulfate (13 Escherichia coli strains were cultured in LB medium (34). Construction of the TE II expression plasmids.…”

Section: Methodsmentioning

confidence: 99%

Type II Thioesterase ScoT, Associated with Streptomyces coelicolor A3(2) Modular Polyketide Synthase Cpk, Hydrolyzes Acyl Residues and Has a Preference for Propionate

Kotowska

Pawlik

Smulczyk-Krawczyszyn

et al. 2009

Appl Environ Microbiol

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Type II thioesterases (TE IIs) were shown to maintain the efficiency of polyketide synthases (PKSs) by removing acyl residues blocking extension modules. However, the substrate specificity and kinetic parameters of these enzymes differ, which may have significant consequences when they are included in engineered hybrid systems for the production of novel compounds. Here we show that thioesterase ScoT associated with polyketide synthase Cpk from Streptomyces coelicolor A3(2) is able to hydrolyze acetyl, propionyl, and butyryl residues, which is consistent with its editing function. This enzyme clearly prefers propionate, in contrast to the TE IIs tested previously, and this indicates that it may have a role in control of the starter unit. We also determined activities of ScoT mutants and concluded that this enzyme is an ␣/␤ hydrolase with Ser90 and His224 in its active site.

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“…N-Acetylcysteamine was supplied by Aldrich, and dodecanoyl-CoA (5a), curcumin (3e), hexanoylCoA (4a), malonyl-CoA, methylmalonyl-CoA, octadecanoylCoA (6a), and succinyl-CoA were purchased from Sigma. 4-Coumaroyl-CoA (1a), cinnamoyl-CoA (2a), and feruloylCoA (3a) were synthesized by the procedure of Blecher (10), and cinnamoyl-diketide-N-acetylcysteamine (NAC) (2f) and 3-oxo-octanoyl-NAC (4f) were synthesized according to a published report (11). 3-Oxo-5-phenyl-pent-4-enoic acid (2d) and 3-oxo-octanoic acid (4d) were synthesized according to the methods of Matsumura et al (12) tively, with modifications.…”

Section: Methodsmentioning

confidence: 99%

In Vitro Synthesis of Curcuminoids by Type III Polyketide Synthase from Oryza sativa

Katsuyama

Matsuzawa

Funa

et al. 2007

Journal of Biological Chemistry

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Synthesis of β-keto and α,β-unsaturated N-acetylcysteamine thioesters

Cited by 45 publications

References 11 publications

Identification and characterization of multiple curcumin synthases from the herb Curcuma longa

Identification and characterization of multiple curcumin synthases from the herb Curcuma longa

Type II Thioesterase ScoT, Associated with Streptomyces coelicolor A3(2) Modular Polyketide Synthase Cpk, Hydrolyzes Acyl Residues and Has a Preference for Propionate

In Vitro Synthesis of Curcuminoids by Type III Polyketide Synthase from Oryza sativa

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