Isolation, identification, and synthesis of 2-carboxyarabinitol 1-phosphate, a diurnal regulator of ribulase-bisphosphate carboxylase activity
The diurnal change in activity of ribulose 1,5-bisphosphate (Rbu-1,5-P/sub 2/) carboxylase (3-phospho-D-glycerate carboxy-lyase (dimerizing); EC 4.1.1.39) of leaves of Phaseolus vulgaris is regulated (in part) by mechanisms that control the level of an endogenous inhibitor that binds tightly to the activated (carbamoylated) form of Rbu-1,5-P/sub 2/ carboxylase. This inhibitor was extracted from leaves and copurified with the Rbu-1,5-P/sub 2/ carboxylase of the leaves. Further purification by ion-exchange chromatography, adsorption to purified Rbu-1,5-P/sub 2/ carboxylase, barium precipitation, and HPLC separation yielded a phosphorylated compound that was a strong inhibitor of Rbu-1,5-P/sub 2/ carboxylase. The compound was analyzed by GC/MS, /sup 13/C NMR, and /sup 1/H NMR and shown to be 2-carboxyarabinitol 1-phosphate ((2-C-phosphohydroxymethyl)-D-ribonic acid). The structure of the isolated compound differs from the Rbu-1,5-P/sub 2/ carboxylase transition-state analogue 2-carboxyarabinitol 1,5-bisphosphate only by the lack of the C-5 phosphate group. This difference results in a higher binding constant for the monophosphate compared with the bisphosphate. The less tightly bound compound acts in a light-dependent, reversible regulation of Rbu-1,5-P/sub 2/ carboxylase activity in vivo.
- Research Organization:
- Carnegie Institution of Washington, Stanford, CA
- OSTI ID:
- 6371023
- Journal Information:
- Proc. Natl. Acad. Sci. U.S.A.; (United States), Vol. 84:3
- Country of Publication:
- United States
- Language:
- English
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Related Subjects
CARBOXY-LYASES
DAILY VARIATIONS
ENZYME INHIBITORS
BIOSYNTHESIS
NUCLEAR MAGNETIC RESONANCE
CARBON 13
ENZYME ACTIVITY
ENZYME INDUCTION
GAS CHROMATOGRAPHY
MASS SPECTROSCOPY
PHASEOLUS
PHOTOSYNTHESIS
PROTONS
BACTERIA
BARYONS
CARBON ISOTOPES
CARBON-CARBON LYASES
CHEMICAL REACTIONS
CHROMATOGRAPHY
ELEMENTARY PARTICLES
ENZYMES
EVEN-ODD NUCLEI
FERMIONS
GENE REGULATION
HADRONS
ISOTOPES
LEGUMINOSAE
LIGHT NUCLEI
LYASES
MAGNETIC RESONANCE
MICROORGANISMS
NUCLEI
NUCLEONS
PHOTOCHEMICAL REACTIONS
PLANTS
RESONANCE
RHIZOBIUM
SEPARATION PROCESSES
SPECTROSCOPY
STABLE ISOTOPES
SYNTHESIS
VARIATIONS
550601* - Medicine- Unsealed Radionuclides in Diagnostics