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| {{STRUCTURE_2og6| PDB=2og6 | SCENE= }} | | {{STRUCTURE_2og6| PDB=2og6 | SCENE= }} |
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| '''Crystal structure of asparagine oxygenase in complex with Fe(II)'''
| | ===Crystal structure of asparagine oxygenase in complex with Fe(II)=== |
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| ==Overview==
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| Non-ribosomally synthesized lipopeptide antibiotics of the daptomycin type are known to contain unnatural beta-modified amino acids, which are essential for bioactivity. Here we present the biochemical and structural basis for the incorporation of 3-hydroxyasparagine at position 9 in the 11-residue acidic lipopeptide lactone calcium-dependent antibiotic (CDA). Direct hydroxylation of l-asparagine by AsnO, a non-heme Fe(2+)/alpha-ketoglutarate-dependent oxygenase encoded by the CDA biosynthesis gene cluster, was validated by Fmoc derivatization of the reaction product and LC/MS analysis. The 1.45, 1.92, and 1.66 A crystal structures of AsnO as apoprotein, Fe(2+) complex, and product complex, respectively, with (2S,3S)-3-hydroxyasparagine and succinate revealed the stereoselectivity and substrate specificity of AsnO. The comparison of native and product-complex structures of AsnO showed a lid-like region (residues F208-E223) that seals the active site upon substrate binding and shields it from sterically demanding peptide substrates. Accordingly, beta-hydroxylated asparagine is synthesized prior to its incorporation into the growing CDA peptide. The AsnO structure could serve as a template for engineering novel enzymes for the synthesis of beta-hydroxylated amino acids.
| | The line below this paragraph, {{ABSTRACT_PUBMED_17373765}}, adds the Publication Abstract to the page |
| | (as it appears on PubMed at http://www.pubmed.gov), where 17373765 is the PubMed ID number. |
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| | {{ABSTRACT_PUBMED_17373765}} |
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| ==About this Structure== | | ==About this Structure== |
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| [[Category: Beta-hydroxylated amino acid]] | | [[Category: Beta-hydroxylated amino acid]] |
| [[Category: Nonribosomal peptide synthesis]] | | [[Category: Nonribosomal peptide synthesis]] |
| ''Page seeded by [http://oca.weizmann.ac.il/oca OCA ] on Sun May 4 10:50:31 2008'' | | |
| | ''Page seeded by [http://oca.weizmann.ac.il/oca OCA ] on Sun Jul 27 17:07:37 2008'' |
