Difference between revisions of "Glycerophosphate"
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|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. The mitochondrial [[Glycerophosphate dehydrogenase complex]] oxidizes glycerophosphate to dihydroxyacetone phosphate and feeds electrons directly to ubiquinone. | |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. The mitochondrial [[Glycerophosphate dehydrogenase complex]] oxidizes glycerophosphate to dihydroxyacetone phosphate and feeds electrons directly to ubiquinone. | ||
}} | }} | ||
{{MitoPedia topics | {{MitoPedia topics | ||
|mitopedia topic=Substrate and metabolite | |mitopedia topic=Substrate and metabolite | ||
}} | }} | ||
== Nomenclature == | == Nomenclature == | ||
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. | :::: 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. | ||
== Source == | == Source == | ||
Recommendation by [[Hoppel CL |Chuck Hoppel]], Director, Ctr Mitochondrial Diseases; Professor, Dept Pharmacology, Case Western Reserve Univ, Cleveland, Ohio - [[US OH Cleveland Hoppel CL]]: | :::: Recommendation by [[Hoppel CL |Chuck Hoppel]], Director, Ctr Mitochondrial Diseases; Professor, Dept Pharmacology, Case Western Reserve Univ, Cleveland, Ohio - [[US OH Cleveland Hoppel CL]]: | ||
:* [http://www.sigmaaldrich.com/catalog/search?term=94124&interface=All&N=0&mode=match%20partialmax&lang=en®ion=LV&focus=product 94124 Sigma sn-Glycerol 3-phosphate lithium salt], ≥95.0% (TLC) Synonym: D-Glycerol 1-phosphate lithium salt, L-Glycerol 3-phosphate lithium salt. MSDS. CAS Number 17989-41-2 (free acid) Empirical Formula (Hill Notation) C<sub>3</sub>H<sub>9</sub>O<sub>6</sub>P · xLi+, Molecular Weight 172.07 (free acid basis). | ::::* [http://www.sigmaaldrich.com/catalog/search?term=94124&interface=All&N=0&mode=match%20partialmax&lang=en®ion=LV&focus=product 94124 Sigma sn-Glycerol 3-phosphate lithium salt], ≥95.0% (TLC) Synonym: D-Glycerol 1-phosphate lithium salt, L-Glycerol 3-phosphate lithium salt. MSDS. CAS Number 17989-41-2 (free acid) Empirical Formula (Hill Notation) C<sub>3</sub>H<sub>9</sub>O<sub>6</sub>P · xLi+, Molecular Weight 172.07 (free acid basis). | ||
== Application in HRR == | == Application in HRR == | ||
'''Gp: Glycerol 3-phosphate ''' sn-Glycerol 3-phosphate bis(cyclohexylammonium) salt; '''Sigma G7886''', store at -20 °C; '''FW = 370.42''' | ::: '''Gp: Glycerol 3-phosphate ''' sn-Glycerol 3-phosphate bis(cyclohexylammonium) salt; '''Sigma G7886''', store at -20 °C; '''FW = 370.42''' | ||
'''Preparation of 1 M stock solution''' (dissolved in H<sub>2</sub>O): | :::: '''Preparation of 1 M stock solution''' (dissolved in H<sub>2</sub>O): | ||
:: | ::::# Weigh 370 mg of Gp and dissolve in 1 ml H<sub>2</sub>O. | ||
::4. Divide into 0.2 ml portions. | ::4. Divide into 0.2 ml portions. | ||
::5. Store frozen at -20 °C. | ::5. Store frozen at -20 °C. | ||
'''Gp: Glycerol 3-phosphate ''' (sn-Glycerol 3-phosphate lithium salt, C<sub>3</sub>H<sub>9</sub>O<sub>6</sub>P • xLi+); '''Sigma 94124''', store at -20 °C; '''FW = 172.07 (free acid basis)'''. | ::: '''Gp: Glycerol 3-phosphate ''' (sn-Glycerol 3-phosphate lithium salt, C<sub>3</sub>H<sub>9</sub>O<sub>6</sub>P • xLi+); '''Sigma 94124''', store at -20 °C; '''FW = 172.07 (free acid basis)'''. | ||
'''Preparation of 1 M stock solution''' (dissolved in H<sub>2</sub>O): | :::: '''Preparation of 1 M stock solution''' (dissolved in H<sub>2</sub>O): | ||
:: | ::::# Weigh 860.35 mg of Gp and dissolve in 3 ml H<sub>2</sub>O. | ||
:: | ::::# Check pH and adjust to 7.0 if necessary with 1 N HCl. | ||
:: | ::::# Transfer to 5 ml volumetric glass flask and adjust the final volume to 5 ml. | ||
:: | ::::# Divide into 0.5 ml portions. | ||
:: | ::::# Store frozen at -20 °C. | ||
'''Oxygraph-2k manual titrations''' [[MiPNet09.12 O2k-Titrations]] | ::: '''Oxygraph-2k manual titrations''' [[MiPNet09.12 O2k-Titrations]] | ||
::* Titration volume: 20 µl using a 50 µl syringe (2 ml O2k-chamber). | ::::* 1 M stock solution. | ||
::* Final concentration: 10 mM. | ::::* Titration volume: 20 µl using a 50 µl syringe (2 ml O2k-chamber). | ||
::::* Final concentration in the O2k-Chamber: 10 mM. | |||
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 vary, requiring further adjustments. | :::: 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 vary, requiring further adjustments. | ||
Revision as of 06:45, 14 July 2016
Description
Glycerophosphate (synonym: α-glycerophosphate; glycerol-3-phosphate; C3H9O6P) is an organophosphate and it is a component of glycerophospholipids. The mitochondrial Glycerophosphate dehydrogenase complex oxidizes glycerophosphate to dihydroxyacetone phosphate and feeds electrons directly to ubiquinone.
Abbreviation: Gp
MitoPedia topics:
Substrate and metabolite
Nomenclature
- 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.
Source
- Recommendation by Chuck Hoppel, Director, Ctr Mitochondrial Diseases; Professor, Dept Pharmacology, Case Western Reserve Univ, Cleveland, Ohio - US OH Cleveland Hoppel CL:
- 94124 Sigma sn-Glycerol 3-phosphate lithium salt, ≥95.0% (TLC) Synonym: D-Glycerol 1-phosphate lithium salt, L-Glycerol 3-phosphate lithium salt. MSDS. CAS Number 17989-41-2 (free acid) Empirical Formula (Hill Notation) C3H9O6P · xLi+, Molecular Weight 172.07 (free acid basis).
- Recommendation by Chuck Hoppel, Director, Ctr Mitochondrial Diseases; Professor, Dept Pharmacology, Case Western Reserve Univ, Cleveland, Ohio - US OH Cleveland Hoppel CL:
Application in HRR
- Gp: Glycerol 3-phosphate sn-Glycerol 3-phosphate bis(cyclohexylammonium) salt; Sigma G7886, store at -20 °C; FW = 370.42
- Preparation of 1 M stock solution (dissolved in H2O):
- Weigh 370 mg of Gp and dissolve in 1 ml H2O.
- 4. Divide into 0.2 ml portions.
- 5. Store frozen at -20 °C.
- Gp: Glycerol 3-phosphate (sn-Glycerol 3-phosphate lithium salt, C3H9O6P • xLi+); Sigma 94124, store at -20 °C; FW = 172.07 (free acid basis).
- Preparation of 1 M stock solution (dissolved in H2O):
- Weigh 860.35 mg of Gp and dissolve in 3 ml H2O.
- Check pH and adjust to 7.0 if necessary with 1 N HCl.
- Transfer to 5 ml volumetric glass flask and adjust the final volume to 5 ml.
- Divide into 0.5 ml portions.
- Store frozen at -20 °C.
- Oxygraph-2k manual titrations MiPNet09.12 O2k-Titrations
- 1 M stock solution.
- Titration volume: 20 µl using a 50 µl syringe (2 ml O2k-chamber).
- Final concentration in the O2k-Chamber: 10 mM.
- 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 vary, requiring further adjustments.