Titre du document / Document title

(2R)-2-amino-6-hydroxy-4-hexynoic acid, and related amino acids in the fruiting bodies of Amanita miculifera

Auteur(s) / Author(s)

HATANAKA S.-I. ⁽¹⁾ ; NIIMURA Y. ⁽²⁾ ; TAKISHIMA K. ⁽³⁾ ; SUGIYAMA J. ⁽⁴⁾ ;

Affiliation(s) du ou des auteurs / Author(s) Affiliation(s)

⁽¹⁾ Department of Biology, Division of Natural Sciences, International Christian University, Osawa 3-10-2, Mitaka-shi, Tokyo 181, JAPON
⁽²⁾ Radioisotope Research Center, Teikyo University School of Medicine, Kaga 2-11-1, Itabashi-ku, Tokyo 173, JAPON
⁽³⁾ Department of Biochemistry I, National Defense Medical College, Tokorozawa, Saitama 359, JAPON
⁽⁴⁾ Institute of Molecular and Cellular Biosciences, The University of Tokyo, Yayoi 1-1-1, Bunkyo-ku, Tokyo 113, JAPON

Résumé / Abstract

(2R)-2-amino-6-hydroxy-4-hexynoic acid, (2RS)-2-amino-4,5-hexadienoic acid, (2S)-2-amino-4-hexynoic acid, and 2-amino-5-chloro-5-hexenoic acid were isolated and characterised from the fruit bodies of Amanita miculifera, with the first and the last mentioned amino acids being new natural products. Their structures were based on analysis of the results from elementary analysis, oxidation with KMnO₄, determination of optical rotations, ¹H NMR-spectra, and hydrogenation over Adams or Lindlar catalysts. (2RS)-2-Amino-6-hydroxy-4-hexynoic acid was synthesized and optically resolved by renal acylase to confirm its natural (2R)-configuration. The configuration at C-2 of 2-amino-4,5-hexadienoic acid was also assumed from its ORD spectrum, as well as that of its hydrogenation product. The optical rotation (2-amino-5-chloro-5-hexenoic acid) was not determined because it was isolated in trace amounts; it was also prepared from 2-amino-5-hexynoic acid, although in very low yield. A possible biosynthetic route leading to the non-protein amino acids in this fungus is presented.

Revue / Journal Title

Phytochemistry   ISSN 0031-9422 

Source / Source

1998, vol. 49, n^o2, pp. 573-578 (16 ref.)

Langue / Language

Anglais

Editeur / Publisher

Elsevier, Amsterdam, PAYS-BAS  (1961) (Revue)

Mots-clés anglais / English Keywords

Aminoacid ; Isolation ; Molecular structure ; Configuration ; Biosynthesis ; Basidiomycetes ; Fungi ; Thallophyta ;

Mots-clés français / French Keywords

Aminoacide ; Isolement ; Structure moléculaire ; Configuration ; Biosynthèse ; Amanita miculifera ; Basidiomycetes ; Fungi ; Thallophyta ;

Mots-clés espagnols / Spanish Keywords

Aminoácido ; Aislamiento ; Estructura molecular ; Configuración ; Biosíntesis ; Basidiomycetes ; Fungi ; Thallophyta ;

Localisation / Location

INIST-CNRS, Cote INIST : 9408, 35400007092332.0350