N-benzoyl-L-aspartic acid

• CAT Number: I030520
• CAS Number: 4631-12-3
• Molecular Formula: C11H11NO5
• Molecular Weight: 237.21
• Purity: ≥95%
• Synonyms: (2S)-2-benzamidobutanedioic acid
• InChI: InChI=1S/C11H11NO5/c13-9(14)6-8(11(16)17)12-10(15)7-4-2-1-3-5-7/h1-5,8H,6H2,(H,12,15)(H,13,14)(H,16,17)/t8-/m0/s1
• InChIKey: DJLTZJGULPLVOA-QMMMGPOBSA-N
• SMILES: C1=CC=C(C=C1)C(=O)NC(CC(=O)O)C(=O)O

N-benzoyl-L-aspartic acid, a major metabolite of benzyl glucosinolate, can be used for modification of peptides or proteins[1].
N-benzoyl-L-aspartic acid resists racemisation by aqueous acetic anhydride and evidence is adduced to show that they form internal anhydrides rather than oxazolones under these conditions[2].

Reference

[1]. Friedrichs J, et, al. Novel glucosinolate metabolism in larvae of the leaf beetle Phaedon cochleariae. Insect Biochem Mol Biol. 2020 Sep;124:103431.
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[2]. BARKER CC, et, al. The Dehydration and Racemisation of N-Acyl-L-aspartic Acids by Acetic Anhydride. Journal of the Chemical Society. 1953.