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67376

Sigma-Aldrich

Sodium (R)-homocitrate tribasic

≥90.0%

Synonym(s):

(R)-2-Hydroxy-1,2,4-butanetricarboxylic acid trisodium salt, (R)-Homocitrate trisodium salt

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About This Item

Empirical Formula (Hill Notation):
C7H7Na3O7
CAS Number:
320573-06-6
Molecular Weight:
272.10
MDL number:
MFCD16817602
UNSPSC Code:
12352200
PubChem Substance ID:
329760562
NACRES:
NA.25

assay

≥90.0%

optical activity

[α]/D -11.0±2.0°, c = 0.1 in H2O

impurities

≤15.0% water

SMILES string

[Na+].[Na+].[Na+].O[C@](CCC([O-])=O)(CC([O-])=O)C([O-])=O

InChI

1S/C7H10O7.3Na/c8-4(9)1-2-7(14,6(12)13)3-5(10)11;;;/h14H,1-3H2,(H,8,9)(H,10,11)(H,12,13);;;/q;3*+1/p-3/t7-;;;/m1.../s1

InChI key

SNTBDRNHMPWDFS-LSBIWMFESA-K

Application

(R)-Homocitrate trisodium salt may be used in studies of formation and function of the iron-molybdenum cofactor (FeMo-co) which contains 7Fe, 9S, Mo, R-homocitrate. FeMo-co is essential for nitrogen fixation by nitrogenous organisms.

Biochem/physiol Actions

Important metabolite of lysine biosynthesis, pyruvate and 2-oxocarboxylic acid metabolism, homocitrate is as a sensor of lysine-pathway distress[1], it has a dynamic role during nitrogen fixation[2].

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

pictograms

Exclamation mark
GHS07

signalword

Warning

hcodes

H319

Hazard Classifications

Eye Irrit. 2

Storage Class

13 - Non Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
BCBK5424V
BCBD3996V
BCBD3996

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Marcus C Durrant et al.
The Biochemical journal, 397(2), 261-270 (2006-03-29)
Although it is generally accepted that the active site of nitrogenase is located on the FeMo-cofactor, the exact site(s) of N2 binding and reduction remain the subject of continuing debate, with both molybdenum and iron atoms being suggested as key
Yilin Hu et al.
Proceedings of the National Academy of Sciences of the United States of America, 103(46), 17125-17130 (2006-10-26)
The Fe protein is indispensable for nitrogenase catalysis and biosynthesis. However, its function in iron-molybdenum cofactor (FeMoco) biosynthesis has not been clearly defined. Here we show that the Fe protein can act as a Mo/homocitrate insertase that mobilizes Mo/homocitrate for
L Ma et al.
The Journal of biological chemistry, 269(27), 18007-18015 (1994-07-08)
Here we report the large scale isolation and characterization of a species, designated MoFe cluster, that exhibits an S = 3/2 EPR signal, and the comparison of this entity to isolated FeMo cofactor in N-methylformamide and to the active site
Leonardo Curatti et al.
Proceedings of the National Academy of Sciences of the United States of America, 104(45), 17626-17631 (2007-11-06)
Biological nitrogen fixation, the conversion of atmospheric N2 to NH3, is an essential process in the global biogeochemical cycle of nitrogen that supports life on Earth. Most of the biological nitrogen fixation is catalyzed by the molybdenum nitrogenase, which contains
J Imperial et al.
Biochemistry, 28(19), 7796-7799 (1989-09-19)
(R)-2-Hydroxy-1,2,4-butanetricarboxylic acid [(R)-homocitrate] has been has been recently reported to be an integral constituent of the otherwise thought to be inorganic iron-molybdenum cofactor of dinitrogenase [Hoover, T.R., Imperial, J., Ludden, P.W., & Shah, V.K. (1989) Biochemistry 28,2768-2771]. Different organic acids
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