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

Journal Article · Tue Jul 03 00:00:00 EDT 1984 · Biochemistry; (United States)

DOI:https://doi.org/10.1021/bi00309a026· OSTI ID:5779585

Bates, H A; Kaushal, A; Deng, P N; Sciaky, D

Histopine, an unusual amino acid derivative of histidine isolated from crown gall tumors of sunflowers (Helianthus annus) inoculated with Agrobacterium tumefaciens strain B/sub 6/, was previously assigned the gross structure N-(1-carboxyethyl)histidine. A diastereomeric mixture containing histopine was readily prepared by reductive alkylation of (S)-histidine 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 supports the growth of A. tumefaciens whereas (S)-N-(1-carboxyethyl)-(S)-histidine is inactive.

• Research Organization: State Univ. of New York, Stony Brook
• DOE Contract Number: AC02-76CH00016
• OSTI ID: 5779585
• Journal Information: Biochemistry; (United States), Vol. 23:14
• Country of Publication: United States
• Language: English

Related Subjects

59 BASIC BIOLOGICAL SCIENCES
BACTERIA
INFECTIVITY
HISTIDINE
STRUCTURAL CHEMICAL ANALYSIS
BACTERIAL DISEASES
METABOLITES
NEOPLASMS
STEREOCHEMISTRY
SUNFLOWERS
AMINO ACIDS
AZOLES
CARBOXYLIC ACIDS
DISEASES
HETEROCYCLIC ACIDS
HETEROCYCLIC COMPOUNDS
IMIDAZOLES
INFECTIOUS DISEASES
MICROORGANISMS
ORGANIC ACIDS
ORGANIC COMPOUNDS
ORGANIC NITROGEN COMPOUNDS
PLANTS
550200* - Biochemistry