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An Efficient Synthesis of a Probe for Protein Function: 2,3-Diaminopropionic Acid with Orthogonal Protecting Groups

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Ethan A. Englund, Hosahudya N. Gopi, and Daniel H. Appella*

Department of Chemistry, Northwestern University, Evanston, Illinois 60208

Org. Lett., 2004, 6 (2), pp 213–215

DOI: 10.1021/ol0361599

Publication Date (Web): December 25, 2003

Section:

Amino Acids, Peptides, and Proteins

Abstract

An efficient and cost-effective synthesis of N(α)-Boc₂-N(β)-Cbz-2,3-diaminopropionic acid is reported. The synthesis starts from commercially available N(α)-Boc-Asp(OBn)-OH and employs a Curtius rearrangement to establish the β-nitrogen. Proper protection of the α-nitrogen is essential for the success of the Curtius rearrangement.

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Published In Issue January 22, 2004
Received November 4, 2003

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Letter

An Efficient Synthesis of a Probe for Protein Function: 2,3-Diaminopropionic Acid with Orthogonal Protecting Groups

Abstract

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SciFinder Links

History

Recommend & Share

Related Content

Highly Efficient Stereoconservative Amidation and Deamidation of α-Amino Acids

Catalyst-Free Chemoselective N-tert-Butyloxycarbonylation of Amines in Water

Boc-Protected Amines via a Mild and Efficient One-Pot Curtius Rearrangement

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