期刊
AMINO ACIDS
卷 51, 期 7, 页码 991-998出版社
SPRINGER WIEN
DOI: 10.1007/s00726-019-02730-5
关键词
Iminosugars; Amino acid; Stevia; beta-Galactosidase; alpha-Galactosidase; Hydroxy proline; Iminosugar acid; Sugar amino acids
资金
- Fundacion Ramon Areces
- Japanese Society for the Promotion of Science (JSPS KAKENHI) [JP17K08362]
DMDP acetic acid [N-carboxymethyl-2,5-dideoxy-2,5-imino-d-mannitol] 5 from Stevia rebaudiana is the first isolated natural amino acid derived from iminosugars bearing an N-alkyl acid side chain; it is clear from GCMS studies that such derivatives with acetic and propionic acids are common in a broad range of plants including mulberry, Baphia, and English bluebells, but that they are very difficult to purify. Reaction of unprotected pyrrolidine iminosugars with aqueous glyoxal gives the corresponding N-acetic acids in very high yield; Michael addition of both pyrrolidine and piperidine iminosugars and that of polyhydroxylated prolines to tert-butyl acrylate give the corresponding N-propionic acids in which the amino group of beta-alanine is incorporated into the heterocyclic ring. These easy syntheses allow the identification of this new class of amino acid in plant extracts and provide pure samples for biological evaluation. DMDP N-acetic and propionic acids are potent alpha-galactosidase inhibitors in contrast to potent beta-galactosidase inhibition by DMDP.
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