Synthesis of -Vinyl Amino Acids
互联网
668
This chapter presents procedures for the synthesis of α-vinyl amino acids, in which the usual α-proton is replaced by an unsubstituted vinyl group (Fig. 1 ). The parent member of this family, α-vinylglycine (R≠H), is a natural product ( 1 , 2 ) and acts as a suicide substrate for a number of PLP-dependent enzymes ( 4 – 9 ). Higher members of this family (R≠H) have also been synthesized ( 10 – 12 ). Several including α-vinyl- m -tyrosine ( 13 – 15 ), α-vinyl-DOPA ( 13 – 15 ), α-vinylglutamate ( 16 ), α-vinylornithine ( 17 ), α-vinyllysine ( 18 ), and α-vinylarginine ( 18 ) are Trojan horse inhibitors of their cognate amino acid decarboxylases (AADCs). Such (appropriately labeled) AADC inhibitors may also have potential as reagents for positron emission tomography ( 19 ).
Fig. 1. Generic structure for α-vinyl amino acids.
![[(1S)-1-[[(2S)-2-[[(2S)-5-amino-2-[[(2S)-2-[[(2S)-2-(6-aminohexanoylamino)-3-phenylpropanoyl]amino]-3-hydroxypropanoyl]amino]-5-oxopentanoyl]amino]hexanoyl]amino]-4-bromobutyl]boronic acid，Moligand™，阿拉丁](https://img1.dxycdn.com/p/s14/2024/0619/722/0483842343985733081.jpg!wh200)
![tert-butyl N-[(1R,2S)-1-(cyclopropylsulfonylcarbamoyl)-2-vinyl-cyclopropyl]carbamate，630421-48-6，≥97%，阿拉丁](https://img1.dxycdn.com/p/s14/2024/0619/442/2156925182155633081.jpg!wh200)
