Publisher SummaryThis chapter discusses the chemical synthesis of lactyl CoA, malonyl CoA, and β-ketoöctanoyl CoA. These three compounds are examples of CoA thiolesters that are difficult or impossible to synthesize by the usual thiolester preparative procedures because of interference by α-hy...
SummaryHomogenates were prepared from three sources, Mycobacterium smegmatis Saccharomyces cerevisiae and Escherichia coli and tested for docosyl malonyl-CoA-ACP transacylase activity, using ACP purified from E. coli strain B and [2R, 2S, 1, 3-14C2] docosyl malonyl-CoA synthesized chemically, as...
Publisher SummaryThis chapter discusses analogs involving the replacement of the sulfur of pantetheine, 4'-phosphopantetheine, and coenzyme A with other atoms. In recent years, several analogs of coenzyme A and of some of its component building blocks have been synthesized. Presumably, anti...
Acetyl coenzyme A carboxylase (ACCase), the target site inhibited by two groups of herbicides, the aryloxyphenoxypropionates and cyclohexanediones, was extracted and partially purified from rice (Oryza sativa LeMont L.), barnyardgrass (Echinchloa crusgalli (L.) Beauv.) and sprangletop (Leptochlo...
A method for the synthesis of [14C]malonyl-Coenzyme A starting with 10 μmol of [14C]malonate is reported. The synthesis is accomplished with yields of 48 ± 4% (1σ, n = 6) using a procedure which does not require the isolation or purification of any intermediates.
We present a validated high-performance liquid chromatography/mass spectrometry (HPLC/MS) method for the quantification of malonyl-coenzyme A (CoA) in tissues. The assay consists of extraction of malonyl-CoA from tissue using 10% trichloroacetic acid, isolation using a reversed-phase solid-phase...
Two isomers of malonyl-coenzyme A (malonyl-CoA) were detected in a commercial preparation of malonyl-CoA. These compounds were separated by preparative high-performance liquid chromatography (HPLC) and characterized by HPLC/ultraviolet (UV)/mass spectrometry. Both compounds had a UV absorbance m...
Catalytic transformation of serine-O-carbonate to S-aryl cysteine derivatives was successfully achieved in the presence of Li+ by the use of a pyridoxal model compound having an ionophore function, which is the first example mimicking cystathionine β-synthase, artificially.
Background: Plant nonspecific lipid-transfer proteins (nsLTPs) bind a variety of very different lipids in vitro, including phospholipids, glycolipids, fatty acids and acyl coenzyme As. In this study we have determined the structure of a nsLTP complexed with palmitoyl coenzyme A (PCoA) in order t...
SummaryThe mechanisms underlying the formation of acyl protein modifications remain poorly understood. By investigating the reactivity of endogenous acyl-CoA metabolites, we found a class of acyl-CoAs that undergo intramolecular catalysis to form reactive intermediates that non-enzymatically mod...
Nicotinamide adenine dinucleotide (NADH) is a coenzyme involved in enzyme-catalyzed oxidation-reduction reactions in which a hydride ion is transferred to the substrate or vice versa As part of a broader theoretical study designed to elucidate the mechanism of the hydride-ion transfer, ab initio...
SummaryA genomic library of Streptomyces cattleya was screened to isolate a gene cluster encoding enzymes responsible for the production of fluorine-containing metabolites. In addition to the previously described fluorinase FlA which catalyzes the formation of 5′-fluoro-5′-deoxyadenosine from ...
A series of heterocyclic donor-acceptor systems were synthesized and well characterized by using 1H, 13C NMR, FT-IR, and elemental analysis. They were designed to investigate the effect of thiophene and cyanoacrylic acid number units on the thermal, optical, electrochemical and finally photovolt...
Treatment of readily available chiral building block 1 with (2R)-2,3-O-isopropylideneglyceraldehyde (5) provides a new route for asymmetric synthesis of 2,4-disubstituted pyrrolidines. Several proline-amino acid chimeras: proline-leucine, proline-lysine, proline-arginine and proline-glutamic aci...
An asymmetric synthesis of N-protected (4S)-4-hydroxy L-glutamic acid diester is described. The key feature of the synthesis is the asymmetric 1,3-dipolar cycloadition of nitrone 4 with 5, which provides stereoselectively the isoxazolidine with the correct stereochemistry suitable for the synthe...
Enantiomerically pure L-erythro- and L-threo-4-fluoroglutamic acids 1a and 1b were conveniently prepared. The key steps in this synthesis relied upon separation of diastereomers of N-chloroacetyl-4-fluoroglutamic acid 5-methyl ester 7 by recrystallization and enzymatic resolution of enantiomers ...
The ionization of fatty acids, fatty amines and N-acylamino acids incorporated in phosphatidylcholine single-walled vesicles has been measured. The guest molecules have been specifically enriched with 13C and titrated by using NMR spectroscopy. The apparent pKa of fatty acids in phosphatidylchol...
Rigid analogs of ACPD have been synthesized to mimick different potential conformations of ACPD in aqueous solution. One of them, (±)-ABHD-I is a competitive antagonist at mGluR1a receptor with a KB value of 300 μM.
A facile stereoselective method for the synthesis of γ-substituted, γ-amino acids from α-amino acids was developed. The key step of the procedure is complete reduction of the keto functionality of α-amino acyl Meldrum's acid by sodium acetoxyborohydride. The resulting amino alkyl Meldru...
In order to assess the manifestation of possible conformations of poly(amino acids) in 13C cross-polarization/magic angle spinning nuclear magnetic resonance (CP/MAS n.m.r.) spectra, the conformational structures of poly(α-l-glutamic acid) (poly(Glu)), of poly(α-L-aspartic acid) (poly(Asp)) an...
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