Synthesis of the functionalizable methionine surrogate azidohomoalanine using Boc-homoserine as precursor.
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.
Link
A James
AJ
Division of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, California 91106, USA. ajlink@princeton.edu
Vink
Mandy K S
MK
Tirrell
David A
DA
D000409:Alanine / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D001671:Biochemistry / Q000379:methods; D002852:Chromatography, Ion Exchange; D003460:Crystallization; D005563:Formic Acid Esters / Q000737:chemistry; D006714:Homoserine / Q000031:analogs & derivatives* / Q000737:chemistry*
D005563:Formic Acid Esters; C506098:azidohomoalanine; C000345:t-butyloxycarbonyl group; C524621:tert-butoxycarbonylhomoserine; D006714:Homoserine; D000409:Alanine