30748-15-3Relevant articles and documents
Further studies on the biosynthesis of the boron-containing antibiotic aplasmomycin
Lee,Dewick,Gorst-Allman,et al.
, p. 5426 - 5432 (1987)
In the biosynthesis of aplasmomycin by Streptomyces griseus, seven atoms of deuterium from C-2 of acetate are incorporated per chain (one each at C-2, -10, and -12 and two each at C-6 and -14) and 4 atoms of oxygen from C-1 of acetate (one each at C-1, -7
Microdomain formation in phosphatidylethanolamine bilayers detected by 2H-NMR
Shin, Kyong-Hwa,Nagamori, Toshiaki,Kimura, Yasuhiro,Tomoi, Masao,Fujiwara, Toshimichi,Akutsu, Hideo
, p. 55 - 62 (1995)
In deuterium NMR spectra of phosphatidylethanolamine bilayers with an extremely high content of saturated fatty acids, each C1 deuteron of the glycerol backbone gave rise to a doublet. This suggests the presence of two backbone conformations, the exchange between which is slow on an NMR time-scale. The origin of the two conformations has been investigated in this work using saturated 1,2-diacyl-sn-glycero-3-phosphoethanolamine specifically deuterated in the glycerol backbone. The results showed that the two conformations originate from different domains, which have different fatty acid compositions. The differential scanning calorimetry of the bilayers suggested that the size of the domain is not large enough to show an independent phase transition. Thus, the formation of microdomains in the phosphatidylethanolamine bilayers has been concluded. Conformational difference in different domains was shown to be restricted to the C1 position of the glycerol backbone. The microdomains of phosphatidylethanolamine were retained even in the presence of other phospholipids.
Vanadium-Catalyzed Deoxydehydration of Glycerol Without an External Reductant
Petersen, Allan R.,Nielsen, Lasse B.,Dethlefsen, Johannes R.,Fristrup, Peter
, p. 769 - 778 (2018/02/27)
A vanadium-catalysed deoxydehydration (DODH) of neat glycerol has been developed. Cheap and readily available ammonium metavanadate (NH4VO3) affords higher yields of allyl alcohol than the well-established catalyst methyltrioxorhenium. A study in which deuterium-labelled glycerol was used was undertaken to further elucidate the dual role of glycerol as both an oxidant and reductant. This study led to the proposal of a metal-catalysed DODH mechanism for the production of allyl alcohol and a deeper understanding of the formation of the byproducts acrolein and propanal.
Assay for the enantiomeric analysis of [2H1]-fluoroacetic acid: Insight into the stereochemical course of fluorination during fluorometabolite biosynthesis in Streptomyces cattleya
O'Hagan, David,Goss, Rebecca J. M.,Meddour, Abdelkrim,Courtieu, Jacques
, p. 379 - 387 (2007/10/03)
A sensitive method for the configurational analysis of (R)- and (S)-[2H1]-fluoroacetate has been developed using 2H{1H}-NMR in a chiral liquid crystalline solvent. This has enabled biosynthetic experiments to be
Site-specific hydrogen isotope fractionation in the biosynthesis of glycerol
Zhang, Ben-Li,Buddrus, Stephan,Martin, Maryvonne L.
, p. 1 - 15 (2007/10/03)
The nuclear magnetic resonance study of site-specific natural isotope fractionation (SNIF-NMR) produced in the glycolytic conversion of glucose into ethanol and glycerol provides isotopic transfer coefficients, a(ij), which relate sites i in the products to sites j in the reactants. The isotopic connection between the carbon-bound hydrogens of glycerol and those of glucose and water in fermentation reactions carried out with Saccharomyces cerevisiae has been investigated. The a(ij) coefficients provide mechanistic information on the genealogy of the glycerol hydrogens, on the relative rates of triose phosphate isomerization and reduction of dihydroxyacetone phosphate into glycerol 3-phosphate, on the stereospecificity of the reduction, on the percentages of intra- and intermolecular hydrogen transfer occurring in the course of the reaction, and on the order of magnitude of the active overall kinetic and thermodynamic isotope effects. Thus a close connection is determined between sites 3 pro-R of glycerol (stereospecific numbering) and H6 pro-R and to a lesser extent H2 of glucose and between site 3 pro-S of glycerol and H6 pro-S and H1 of glucose. Moreover site 2 of glycerol, which exhibits a strong correlation with water is also partly connected with glucose. Possible changes in the values of the isotopic transfer coefficients, as a function of the composition of the medium or of the environmental conditions, enable mechanistic perturbations such as variations in the percentage of intermolecular transfers to be detected. Analyzed in terms of stereospecificity of the reduction step the isotopic results provide a direct chemical shift assignment of the enantiomeric pairs (1(S), 3(R)) and (1(R), 3(S)) of glycerol triacetate. The influence of added bisulfite, which strongly increases the yield in glycerol is estimated. The isotopic characterization of the bioconversion producing both ethanol and glycerol has been extended to the determination of the carbon isotopic parameters by isotope ratio mass spectrometry. Although it usually occurs as a byproduct of the fermentation, glycerol can be considered as a useful complementary probe for characterizing the glycolytic pathway and for inferring various properties of the carbohydrate precursors. (C) 2000 Academic Press.
