Difference between revisions of "Glycerophosphate"
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{{MitoPedia | {{MitoPedia | ||
|abbr=Gp | |abbr=Gp | ||
|description='''Glycerophosphate''' (synonym: α-glycerophosphate; glycerol-3-phosphate; C<sub>3</sub>H<sub>9</sub>O<sub>6</sub>P) is an organophosphate and it is a component of glycerophospholipids. | |description='''Glycerophosphate''' (synonym: α-glycerophosphate; glycerol-3-phosphate; C<sub>3</sub>H<sub>9</sub>O<sub>6</sub>P) is an organophosphate and it is a component of glycerophospholipids. [[Glycerophosphate dehydrogenase complex]] oxidizes glycerophosphate to dihydroxyacetone phosphate and feeds electrons directly to ubiquinone. See also [http://en.wikipedia.org/wiki/Glycerol_3-phosphate_shuttle glycerol phosphate shuttle]. | ||
|type=Respiration | |type=Respiration | ||
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== Nomenclature issues == | == Nomenclature issues == | ||
Revision as of 10:28, 14 December 2014
Description
Glycerophosphate (synonym: α-glycerophosphate; glycerol-3-phosphate; C3H9O6P) is an organophosphate and it is a component of glycerophospholipids. Glycerophosphate dehydrogenase complex oxidizes glycerophosphate to dihydroxyacetone phosphate and feeds electrons directly to ubiquinone. See also glycerol phosphate shuttle.
Abbreviation: Gp
MitoPedia topics: Substrate and metabolite
Nomenclature issues
Due to an ambiguity in the D,L nomenclature based on the Fisher projection the biologically active enantiomer can be labeled either D-glycerol 1-phosphate or L-glycerol 3-phosphate. Alternatives are sn-glycerol 3-phosphate or DL-alpha-glycerophosphate. Following the Cahn–Ingold–Prelog priority rules, the biologically active substance is always the (R) enantiomer, independent of whether the substance is called glycerol 1-phosphate or glycerol 3-phosphate.
Availability
Sigma does not sell DL-alpha-glycerophosphate disodium salt hexahydrate (FW = 324.1; Sigma G-2138, CAS# 1555-56-2 (anhydrous)) any more (personal communication with Dr. Zdenek Drahota, Dept. of Bioenergetics, Institute of Physiology, Academy of Sciences of the Czech Rep.)!
In Dr. Drahota's lab a 1 M stock solution is used and the final concentration in the O2k-Chamber is 10 mM.
Search for an adequate replacement is underway.
Alternatives:
- Racemic disodium salt hexahydrate: CAS#: 3325-00-6, "identical" (not considering purity) to the discontinued Sigma product mentioned above, but actual availability would have to be checked with each individual supplier
- CHEMOS: 151924
- BOC Sciences: 3325-00-6 (sic!, they use CAS numbers as their product numbers, which actually makes a lot of sense).
- Advance Scientific & Chemical: G2218.
- Racemic magnesium salt: AppliChem: A4558,1000
- Enantiopure lithium salt: Sigma: 94124
- Enatiopure bis(cyclohexylammonium) salt: Sigma: G7886
If a racemic mixture (like Sigma G-2138) is replaced by the biologically active enantiomer the amount of substance (measured in moles) usually has to be halved. However, also consider that stated purities may be different, requiring further adjustments.