534-00-9Relevant articles and documents
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Heller
, p. 4858 (1952)
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Synthesis and mass spectra of rearrangement bio-signature metabolites of anaerobic alkane degradation via fumarate addition
Chen, Jing,Zhou, Lei,Liu, Yi-Fan,Hou, Zhao-Wei,Li, Wei,Mbadinga, Serge Maurice,Zhou, Jing,Yang, Tao,Liu, Jin-Feng,Yang, Shi-Zhong,Wu, Xiao-Lin,Gu, Ji-Dong,Mu, Bo-Zhong
, (2020/05/01)
Metabolite profiling in anaerobic alkane biodegradation plays an important role in revealing activation mechanisms. Apart from alkylsuccinates, which are considered to be the usual biomarkers via fumarate addition, the downstream metabolites of C-skeleton rearrangement can also be regarded as biomarkers. However, it is difficult to detect intermediate metabolites in both environmental samples and enrichment cultures, resulting in lacking direct evidence to prove the occurrence of fumarate addition pathway. In this work, a synthetic method of rearrangement metabolites was established. Four compounds, namely, propylmalonic acid, 2-(2-methylbutyl)malonic acid, 2-(2-methylpentyl)malonic acid and 2-(2-methyloctyl)malonic acid, were synthesized and determined by four derivatization approaches. Besides, their mass spectra were obtained. Four characteristic ions were observed at m/z 133 + 14n, 160 + 28n, 173 + 28n and [M - (45 + 14n)]+ (n = 0 and 2 for ethyl and n-butyl esters, respectively). For methyl esterification, mass spectral features were m/z 132, 145 and [M - 31]+, while for silylation, fragments were m/z 73, 147, 217, 248, 261 and [M - 15]+. These data provide basis on identification of potential rearrangement metabolites in anaerobic alkane biodegradation via fumarate addition.
Straightforward synthesis of all stenusine and norstenusine stereoisomers
Mueller, Tobias,Dettner, Konrad,Seifert, Karlheinz
experimental part, p. 6032 - 6038 (2011/12/15)
All the stereoisomers of stenusine (1) and norstenusine (21) have been efficiently synthesized by the asymmetric hydrogenation of pyridines. The (2R,3S)- and (2R,3R)-isomers of 1, that are difficult to prepare, have been synthesized for the first time using a chemoenzymatic approach in eight steps with an 8 % total yield. All the target compounds were obtained in good stereochemical purity by using very simple and inexpensive reagents and auxiliaries. All the stereoisomers of the defensive alkaloids stenusine and norstenusine produced by Stenus beetles have been synthesized in a straightforward manner. The chiral (S) side chain is derived from (S)-2-methyl-1-butanol. For the difficult preparation of (R)-3-(2-methylbutyl) pyridine, a highly efficient chemoenzymatic approach was developed.
