Neutral thiol as a proximal ligand to ferrous heme iron: Implications for heme proteins that lose cysteine thiolate ligation on reduction

No abstract is available for this paper.

• Publication year

  2003

• Venue

  Proceedings of the National Academy of Sciences of the United States of America

• Publication date

  2003-03-24

• Fields of study

  Medicine, Chemistry

• Identifiers
  DOI 10.1073/pnas.0737142100PMID 12655049PMCID PMC152975
• 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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  1990cited by this paper
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