Glycerophosphate

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Glycerophosphate

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).
  • We tested also Gp: Glycerol 3-phosphate sn-Glycerol 3-phosphate bis(cyclohexylammonium) salt; Sigma G7886, store at -20 °C; FW = 370.42, ≥93.0% (TLC) and obtained similar results.
  • We tested also and currently use rac-Glycerol 1-phosphate disodium salt hexahydrate; from Santa Cruz Biotechnology sc-215789, store at +4°C; FW = 324.13.

Application in HRR

Gp: rac-Glycerol 1-phosphate disodium salt hexahydrate sc-215789', store at +4°C; FW = 324.13
Preparation of 1 M stock solution (dissolved in H2O):
  1. Weigh 324 mg of Gp and dissolve in 1 mL H2O.
  2. Divide into 0.2 mL portions.
  3. 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.


SUITbrowser question: Glycerophosphate pathway

The SUITbrowser can be used to find the best SUIT protocols to analyze the glycerophosphate pathway, among other research questions.


List of publications: CGpDH-linked substrate state