53795-94-1Relevant academic research and scientific papers
RATIONAL SYNTHESIS OF DEUTERIUM-LABELLED PYRIDOXAL AND PYRIDOXAL ALKALOIDS
Bringmann, Gerhard,Schneider, Stephan
, p. 175 - 178 (1986)
A synthesis of pyridoxal is described, which avoids delicate redox reactions at the accomplished pyridoxyl system.This synthesis allows the facile preparation of highly (>98percent) deuterated pyridoxal 10b and of B6-derived alkaloids.
Biosynthesis of the fungal metabolite, piliformic acid (2-hexylidene-3-methylsuccinic acid)
Chesters, Nicola C. J. E.,O'Hagan, David
, p. 827 - 834 (1997)
The biosynthesis of piliformic acid, a secondary metabolite of various xylariaceous fungi, has been studied in Poronia piliformis and Xylaria mali. The metabolite can be retro-biosynthetically cleaved to generate a C8 and a C3 moiety. The study reveals that the C8 unit is derived directly from octanoate and that the octanoate in turn originates from a fatty acid synthase (FAS) rather than from a polyketide synthase (PKS). This conclusion is drawn after assaying the stereochemical course of the enoyl reductase involved in the synthesis of the octanoate unit. The C3 unit is efficiently labelled by succinate and the citric acid cycle intermediate oxaloacetate is implicated as a key biosynthetic precursor. The location of deuterium after isotopic labelling with sodium [2H15]octanoate reveals a 1,3-hydrogen shift, indicative of a double-bond isomerisation, operating at a late stage in the biosynthesis. A hypothesis for piliformic acid biosynthesis is presented and discussed in the context of structurally related fungal and lichen metabolites.
Synthetic method of stable isotope deuterium-labeled alpha-amino acid
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Paragraph 0054; 0058-0059, (2019/12/15)
The invention relates to a synthetic method of stable isotope deuterium-labeled alpha-amino acid. According to the method, one or more deuterium-labeled halides are taken as labeled precursors and subjected to a reaction with phthalimide dimethyl malonate sodium salt, one or more deuterium-substituted phthalimide dimethyl malonate is obtained, and after hydrolysis, stable isotope deuterium-labeledalpha-amino acid is obtained. Compared with the prior art, the synthetic method is simple, safe and reliable, chemical purity of a product after simple separation and purification reaches 99% or higher, isotope abundance is 99% or higher, and the method can be applied to fields of protein metabolism tracing, food safety testing and the like.
Synthesis and screening of stereochemically diverse combinatorial libraries of peptide tertiary amides
Gao, Yu,Kodadek, Thomas
, p. 360 - 369 (2013/06/05)
Large combinatorial libraries of N-substituted peptides would be an attractive source of protein ligands, because these compounds are known to be conformationally constrained, whereas standard peptides or peptoids are conformationally mobile. Here, we report an efficient submonomer solid-phase synthetic route to these compounds and demonstrate that it can be used to create high quality libraries. A model screening experiment and analysis of the hits indicates that the rigidity afforded by the stereocenters is critical for high affinity binding.
The CFTA method: A reliable procedure for the determination of the absolute configuration of chiral primary amines by 1H NMR spectroscopic analysis
Takeuchi, Yoshio,Segawa, Masaru,Fujisawa, Hidehito,Omata, Kenji,Lodwig, Siegfried N.,Unkefer, Clifford J.
, p. 4617 - 4619 (2007/10/03)
Surprisingly stable anti-periplanar conformers of CFTA amides form the basis of a new and very reliable method for determining the absolute configuration of chiral primary amines by 1H NMR spectroscopy (see picture). CFTA = α-cyano-α-fluoro-p-tolylacetic acid. (Chemical Equation Presented).
Measurement of biosynthesis and breakdown rates of biological molecules that are inaccessible or not easily accessible to direct sampling, non-invasively, by label incorporation into metabolic derivatives and catabolitic products
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Page 4, (2008/06/13)
Methods of determining rate of biosynthesis or breakdown of biological molecules from metabolic derivatives and catabolic products are disclosed herein. In particular, methods of measuring the rates of biosynthesis and breakdown of biological molecules inaccessible or not easily accessible to direct sampling by sampling metabolic derivatives and catabolic products in accessible biological samples are disclosed herein.
VIBRATIONAL ANALYSIS OF L-ALANINE AND DEUTERATED ANALOGS
Susi, Heino,Byler, D. Michael
, p. 1 - 12 (2007/10/02)
Raman spectra of the polycrystalline L-alanine analogs CH3CH(NH3+)COO-, CH3CH(ND3+)COO-, CD3(NH3+)COO-, and CD3(ND3+)COO- have been obtained.A normal copordinate analysis is carried out based on the experimental frequencies of the four isotopic analogs and a 34 parameter valence-type force field defined in terms of local symmetry coordinates.The final refinement, in which five stretching force constants are constrained to fixed values obtained from bond length data, results in an average error of 7 cm-1 (0.9percent) for the observed frequencies of the four isotopically substituted molecules.Band assignments are given in terms of the potential energy distribution for local symmetry coordinates.For non-deuterated L-alanine, the vibrations above 1420 cm-1 and below 950 cm-1 may be described as localized group vibrations.By contrast, the eight modes in the middle frequency range, viz. the three skeletal stretching, the COO- symmteric stertching, one NH3+ rocking, the symmetric CH3 deformation, and the two methyne CH deformation vibrations, are very strongly coupled to one another.Some decoupling appears to take place in the perdeutero molecule, and all but five modes can be described as localized group vibrations.
