Schiff bases formed from retinal and phosphatidylethanolamine, phosphatidylserine, ethanolamine or serine
Open accessAbstract
1. Conditions were established for the reaction of retinal with phosphatidylethanolamine, phosphatidylserine, ethanolamine and serine in chloroform, ethanol or ethanol–water solutions to form retinylidene compounds, or Schiff bases. 2. The Schiff bases were reduced to retinyl compounds with sodium borohydride. 3. Absorption maxima and molar extinction coefficients were determined for the various retinylidene and retinyl compounds and for the corresponding coloured products formed by their reaction with antimony trichloride.
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In chloroform/methanol (2:1), N-ret-PE formation has a bimolecular rate constant of about 3.75 × 10-2 M-1 s-1 and its hydrolysis rate is about 7.9 × 10-6 s-1.
“In a test tube, the formation of N-ret-PE in a mixture of chloroform/methanol (2:1) occurs with a bimolecular rate constant of about 3.75 × 10–2 M–1 s–1 while the rate of its hydrolysis is about 7.9 × 10–6 s–1.528”
From Chemistry of the Retinoid (Visual) Cycle (2014) · cites this paper as [528]
Table 1 reports formation and reverse-reaction rate constants for synthetic phosphatidylethanolamine and retinal in chloroform/ethanol (2:1), so it supports the reaction and solvent attributed to the source. Its values for that mixture are 0.161 mM⁻¹ h⁻¹ and 0.0226 h⁻¹—about 4.47 × 10⁻² M⁻¹ s⁻¹ and 6.28 × 10⁻⁶ s⁻¹—not the two rates claimed. The table is in the section headed “25° in the reactions…”; our copy provides no page number. (LLM, conf=0.88)
Experimental — accuracy not yet measuredThe formation and hydrolysis of N-ret-PE is reversible and highly dependent on the presence of water.
“This reversible reaction is highly dependent on the presence of water.”
From Chemistry of the Retinoid (Visual) Cycle (2014) · cites this paper as [528]
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- Authors
- Plack, P. A., & Pritchard, D. J.
- Affiliations
- Natural Environment Research Council (GB)
- ORCID
- Pritchard, D. J.
- Venue
- Biochemical Journal
- Publisher
- Portland Press Ltd.
- Published
- 1969-12-01
- Volume
- 115
- Issue
- 5
- Pages
- 927-934
- ISSN
- 0306-3283 (ISSN-L)
- PMC
- PMC1185235
- OpenAlex
- W70913238
- Cited by
- 19
- References
- 18
- Citations by year
- 2026: 2 · 2023: 2 · 2017: 2 · 2013: 1
- FWCI
- 0.84
- Type
- journal article
- Language
- en
- Open access
- bronze
- doi.org
- Locations
- Biochemical Journal (publishedVersion)
- PubMed Central (publishedVersion)
- PubMed (publishedVersion)
- Topics
- Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › Retinoids in leukemia and cellular processes
- Life Sciences › Neuroscience › Cellular and Molecular Neuroscience › Photoreceptor and optogenetics research
- Physical Sciences › Chemistry › Organic Chemistry › Phosphorus compounds and reactions
- Keywords
- Schiff base, retinal, phosphatidylethanolamine, phosphatidylserine, monoethanolamine, serine, sodium borohydride reduction, absorption spectra, molar absorptivity
- MeSH terms
- Amino Alcohols, Antimony, Kinetics, Phosphatidylethanolamines, Serine, Spectrophotometry, Spectrum Analysis, Vitamin A
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