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Literature summary for 2.5.1.63 extracted from

  • Thompson, S.; Fleming, I.N.; OHagan, D.
    Enzymatic transhalogenation of dendritic RGD peptide constructs with the fluorinase (2016), Org. Biomol. Chem., 14, 3120-3129.
    View publication on PubMed

Application

Application Comment Organism
synthesis substrate tolerance allows a peptide cargo to be tethered to a 5'-chloro-5'-deoxynucleoside substrate for transhalogenation by the enzyme to a 5'-fluoro-5-deoxynucleoside. The reaction is successfully extended from that previously reported for a monomeric cyclic peptide (cRGD) to cargoes of dendritic scaffolds carrying two and four cyclic peptide motifs. The RGD peptide sequence is known to bind upregulated alphaVbeta3 integrin motifs on the surface of cancer cells and it is demonstrated that the fluorinated products have a higher affinity to alphaVbeta3 integrin than their monomeric counterparts. Tolerance of the fluorinase to these large multimeric peptides suggests that the C-2 position of a chlorinated nucleoside represents a site for the attachment of a diverse range of peptide cargos for use in enzymatic fluorination Streptomyces cattleya

Natural Substrates/ Products (Substrates)

Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
S-adenosyl-L-methionine + fluoride Streptomyces cattleya
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5'-deoxy-5'-fluoroadenosine + L-methionine
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r

Organism

Organism UniProt Comment Textmining
Streptomyces cattleya Q70GK9 gene flA
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Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
additional information the enzyme has a specificity tolerance at the 2-position of the adenine base, replacement of hydrogen with an acetylene group at this position gives the modified substrate 5'-chlorodeoxy-2-ethynyladenosine which is an efficient substrate for transhalogenation in the presence of Se-adenosyl-L-selenomethionine. The fluorinase catalyzes a reversible transhalogenation of 5'-chlorodeoxy-2-ethynyladenosine to 5'-fluorodeoxy-2-ethynyladenosine and vice versa using L-selenomethionine and Cl- or F-, respectively. The enzyme is also active in transhalogenation with 5'-chlorodeoxy-2-ethynyladenosine linked to RGD peptides via a PEG linker, overview. The tolerance of the fluorinase to large multimeric peptides suggests that the C-2 position of a chlorinated nucleoside represents a site for the attachment of a diverse range of peptide cargos for use in enzymatic fluorination Streptomyces cattleya ?
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?
S-adenosyl-L-methionine + fluoride
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Streptomyces cattleya 5'-deoxy-5'-fluoroadenosine + L-methionine
-
r

Synonyms

Synonyms Comment Organism
fluorinase
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Streptomyces cattleya