Hydroxylation of limonene enantiomers and analogs by recombinant (-)-limonene 3- and 6-hydroxylases from mint (Mentha) species: evidence for catalysis within sterically constrained active sites.

No abstract is available for this paper.

• Publication year

  2001

• Venue

  Archives of Biochemistry and Biophysics

• Publication date

  2001-03-01

• Fields of study

  Biology, Medicine, Chemistry, Environmental Science

• Identifiers
  DOI 10.1006/ABBI.2000.2248PMID 11368174
• External record

  Open on Semantic Scholar

• Source metadata

  Semantic Scholar, PubMed

• No claims are published for this paper.

• No concepts are published for this paper.

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  1996cited by this paper
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  1995cited by this paper
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  1994cited by this paper
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