Structure and synthesis of histopine, a histidine derivative produced by crown gall tumors.

Histopine, an unusual amino acid derivative of histidine isolated from crown gall tumors of sunflowers (Helianthus annus) inoculated with Agrobacterium tumefaciens strain B6, was previously assigned the gross structure N-(1-carboxyethyl) histidine (2). A diastereomeric mixture containing histopine (2a and 2b) was readily prepared by reductive alkylation of (S)-histidine (1) with pyruvic acid and sodium cyanoborohydride. The individual diastereomers were prepared by reaction of (S)-histidine with (R)- and (S)-2-bromopropionic acid. (R)-N-(1-Carboxyethyl)-(S)-histidine (2a) supports the growth of A. tumefaciens whereas (S)-N-(1-carboxyethyl)-(S)-histidine (2b) is inactive. Therefore, we assign structure 2a to histopine.
AuthorsH A Bates, A Kaushal, P N Deng, D Sciaky
JournalBiochemistry (Biochemistry) Vol. 23 Issue 14 Pg. 3287-90 (Jul 3 1984) ISSN: 0006-2960 [Print] UNITED STATES
PMID6466642 (Publication Type: Journal Article, Research Support, U.S. Gov't, Non-P.H.S., Research Support, U.S. Gov't, P.H.S.)
Chemical References
  • histopine
  • Histidine
  • Chromatography, High Pressure Liquid
  • Histidine (analogs & derivatives, analysis, pharmacology)
  • Plant Tumors (analysis)
  • Rhizobium (drug effects)
  • Stereoisomerism

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