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Chemical Structure| 5381-24-8 Chemical Structure| 5381-24-8

Structure of 5381-24-8

Chemical Structure| 5381-24-8

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Product Citations

Product Citations

Kumar, Vikas ; Johnson, Bryce P. ; Dimas, Dustin A. ; Singh, Shanteri ;

Abstract: The widespread utility of isoprenoids has recently sparked interest in efficient synthesis of isoprene-diphosphate precursors. Current efforts have focused on evaluating two-step "isoprenol pathways," which phosphorylate prenyl alcs. using promiscuous kinases/phosphatases. The convergence on isopentenyl phosphate kinases (IPKs) in these schemes has prompted further speculation about the class's utility in synthesizing non-natural isoprenoids. However, the substrate promiscuity of IPKs in general has been largely unexplored. Towards this goal, authors report the biochem. characterization of five novel IPKs from Archaea and the assessment of their substrate specificity using 58 alkyl-monophosphates. This study reveals the IPK-catalyzed synthesis of 38 alkyl-diphosphate analogs and discloses broad substrate specificity of IPKs. Further, to demonstrate the biocatalytic utility of IPK-generated alkyl-diphosphates, they also highlight the synthesis of alkyl-L-tryptophan derivatives using coupled IPK-prenyltransferase reactions. These results reveal IPK-catalyzed reactions are compatible with downstream isoprenoid enzymes and further support their development as biocatalytic tools for the synthesis of non-natural isoprenoids.

Keywords: alternate mevalonate pathway ; biocatalysis ; enzyme promiscuity ; natural products ; terpenoid

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Product Details of [ 5381-24-8 ]

CAS No. :5381-24-8
Formula : C9H8OS
M.W : 164.22
SMILES Code : OCC1=CSC2=CC=CC=C21
MDL No. :MFCD02682007

Safety of [ 5381-24-8 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H312-H315-H319-H332-H335
Precautionary Statements:P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P330-P332+P313-P337+P313-P362-P403+P233-P405-P501

Application In Synthesis of [ 5381-24-8 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Upstream synthesis route of [ 5381-24-8 ]

[ 5381-24-8 ] Synthesis Path-Upstream   1~1

  • 1
  • [ 5381-24-8 ]
  • [ 1196-19-6 ]
YieldReaction ConditionsOperation in experiment
73% With phosphorus tribromide In diethyl ether at 0 - 20℃; for 1.25 h; B. To a stirred solution of benzothien-3-ylmethanoi (400 mg, 2.44 mmol) in ether (12 ml_) at 00C was added PBr3 (0.23 mL, 2.42 mmol) dropwise. The mixture was stirred at 00C for 30 min. and then at ambient temperature for 45 min. The reaction mixture was poured into a mixture of ice water and ether. The organic phase was separated and washed with brine, dried and concentrated to give 3-(bromomethyl)benzothiophene as a pale solid (404 mg, 73percent).
References: [1] Patent: WO2008/110793, 2008, A1, . Location in patent: Page/Page column 111.
[2] Patent: US2009/176996, 2009, A1, . Location in patent: Page/Page column 15-16.
 

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