Literature DB >> 24180620

Enantioselective synthesis of isotopically labeled homocitric acid lactone.

Jared T Moore1, Nadine V Hanhan, Maximillian E Mahoney, Stephen P Cramer, Jared T Shaw.   

Abstract

A concise synthesis of homocitric acid lactone was developed to accommodate systematic placement of carbon isotopes (specifically (13)C) for detailed studies of this cofactor. This new route uses a chiral allylic alcohol, available in multigram quantities from enzymatic resolution, as a starting material, which transposes asymmetry through an Ireland-Claisen rearrangement.

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Year:  2013        PMID： 24180620      PMCID： PMC3932135          DOI： 10.1021/ol402802g

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  8 in total

1.  New insights into structure-function relationships in nitrogenase: A 1.6 A resolution X-ray crystallographic study of Klebsiella pneumoniae MoFe-protein.

Authors:  S M Mayer; D M Lawson; C A Gormal; S M Roe; B E Smith
Journal:  J Mol Biol       Date:  1999-10-01       Impact factor: 5.469

2.  Enantioselective Syntheses of (-)- and (+)-Homocitric Acid Lactones.

Authors:  Gastón H. Rodríguez R ; Jean-François Biellmann
Journal:  J Org Chem       Date:  1996-03-08       Impact factor: 4.354

Review 3.  Nitrogenase assembly.

Authors:  Yilin Hu; Markus W Ribbe
Journal:  Biochim Biophys Acta       Date:  2012-12-08

Review 4.  Biosynthesis of the iron-molybdenum cofactor of nitrogenase.

Authors:  Yilin Hu; Markus W Ribbe
Journal:  J Biol Chem       Date:  2013-03-28       Impact factor: 5.157

5.  Requirement of nifV gene for production of wild-type nitrogenase enzyme in Klebsiella pneumoniae.

Authors:  P A McLean; R A Dixon
Journal:  Nature       Date:  1981-08-13       Impact factor: 49.962

6.  Crystallographic structure and functional implications of the nitrogenase molybdenum-iron protein from azotobacter vinelandii.

Authors:  J Kim; D C Rees
Journal:  Nature       Date:  1992-12-10       Impact factor: 49.962

7.  Evidence for interstitial carbon in nitrogenase FeMo cofactor.

Authors:  Thomas Spatzal; Müge Aksoyoglu; Limei Zhang; Susana L A Andrade; Erik Schleicher; Stefan Weber; Douglas C Rees; Oliver Einsle
Journal:  Science       Date:  2011-11-18       Impact factor: 47.728

8.  Substrate reduction properties of dinitrogenase activated in vitro are dependent upon the presence of homocitrate or its analogues during iron-molybdenum cofactor synthesis.

Authors:  J Imperial; T R Hoover; M S Madden; P W Ludden; V K Shah
Journal:  Biochemistry       Date:  1989-09-19       Impact factor: 3.162
  8 in total
  2 in total

1.  Asymmetric Synthesis of Homocitric Acid Lactone.

Authors:  Leslie A Nickerson; Valerie Huynh; Edward I Balmond; Stephen P Cramer; Jared T Shaw
Journal:  J Org Chem       Date:  2016-10-21       Impact factor: 4.354

2.  Global Diastereoconvergence in the Ireland-Claisen Rearrangement of Isomeric Enolates: Synthesis of Tetrasubstituted α-Amino Acids.

Authors:  Tyler J Fulton; Alexander Q Cusumano; Eric J Alexy; Yun E Du; Haiming Zhang; K N Houk; Brian M Stoltz
Journal:  J Am Chem Soc       Date:  2020-12-15       Impact factor: 15.419
  2 in total

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