Abstract |
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.
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Authors | H A Bates, A Kaushal, P N Deng, D Sciaky |
Journal | Biochemistry
(Biochemistry)
Vol. 23
Issue 14
Pg. 3287-90
(Jul 03 1984)
ISSN: 0006-2960 [Print] United States |
PMID | 6466642
(Publication Type: Journal Article, Research Support, U.S. Gov't, Non-P.H.S., Research Support, U.S. Gov't, P.H.S.)
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Chemical References |
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Topics |
- Chromatography, High Pressure Liquid
- Histidine
(analogs & derivatives, analysis, pharmacology)
- Plant Tumors
(analysis)
- Rhizobium
(drug effects)
- Stereoisomerism
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