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

Nature Protocols volume 2, pages 1884–1887 (2007)Cite this article

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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Figure 1
Figure 2: Schematic of synthesis of AHA from protected homoserine.

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References

  1. Mangold, J.B., Mischke, M.R. & Lavelle, J.M. Azidoalanine mutagenicity in Salmonella—effect of homologation and alpha-methyl substitution. Mutat. Res. 216, 27–33 (1989).

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  2. Link, A.J., Vink, M.K.S. & Tirrell, D.A. 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

  1. A James Link & Mandy K S Vink

    Present address: 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.).,

Authors and Affiliations

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

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

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  1. Mandy K S Vink
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  2. David A Tirrell
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Correspondence to A James Link.

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The authors declare no competing financial interests.

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Link, A., Vink, M. & Tirrell, D. Synthesis of the functionalizable methionine surrogate azidohomoalanine using Boc-homoserine as precursor. Nat Protoc 2, 1884–1887 (2007). https://doi.org/10.1038/nprot.2007.269

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