Protocol | Published:

Synthesis of the functionalizable methionine surrogate azidohomoalanine using Boc-homoserine as precursor

Nature Protocols volume 2, pages 18841887 (2007) | Download Citation

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Abstract

This protocol describes a synthetic route to the non-canonical amino acid azidohomoalanine (AHA) using protected homoserine as a starting material. An alternative route to AHA is presented in a companion paper. This synthesis can be completed in 5 days.

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References

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    , & Azidoalanine mutagenicity in Salmonella—effect of homologation and alpha-methyl substitution. Mutat. Res. 216, 27–33 (1989).

  2. 2.

    , & Preparation of the functionalizable methionine surrogate azidohomoalanine via copper-catalyzed diazo transfer. Nat. Protoc. 2, 1879–1883 (2007).

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Acknowledgements

This work was supported by NIH, by an NSF graduate fellowship to A.J.L. and by a grant from the Netherlands Organization for Scientific Research to M.K.S.V.

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Author notes

    • A James Link
    •  & Mandy K S Vink

    Present address: Department of Chemical Engineering, Princeton University, A207 Engineering Quadrangle, Princeton, New Jersey 08544, USA (A.J.L.). BioCatalytics Europe GmbH, Parkring 18, A-8074, Grambach, Austria (M.K.S.V.).

Affiliations

  1. Division of Chemistry and Chemical Engineering, California Institute of Technology, MC 210-41, Pasadena, California 91106, USA.

    • A James Link
    • , Mandy K S Vink
    •  & David A Tirrell

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Competing interests

The authors declare no competing financial interests.

Corresponding author

Correspondence to A James Link.

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DOI

https://doi.org/10.1038/nprot.2007.269

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