atRAL can spontaneously react with PE to form NRPE

Stable Identifier
R-HSA-2466846
Type
Reaction [transition]
Species
Homo sapiens
Compartment
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In the disc membranes of photoreceptor outer segments, all-trans-retinal (atRAL) can spontaneously and reversibly react with phosphatidiylethanolamine (PE, cephalin; a phospholipid found in in membranes) to form a Schiff base product, N-retinylidene-phosphatidylethanolamine (NRPE) (Poincelot et al. 1969, Parish et al. 1998, Mata et al. 2000). Then, either NRPE is "flipped" over to the cytoplasmic side of disc membranes by ABCA4 where it can dissociate (thus releasing atRAL to re-enter the retinoid cycle) or it can condense with another atRAL to form a toxic diretinal compound. The route taken is determined by whether a functional ABCA4 protein is present or not.

Literature References
PubMed ID Title Journal Year
5763079 Lipid to protein chromophore transfer in the photolysis of visual pigments

Poincelot, RP, Millar, PG, Kimbel, RL, Abrahamson, EW

Nature 1969
10852960 Biosynthesis of a major lipofuscin fluorophore in mice and humans with ABCR-mediated retinal and macular degeneration

Mata, NL, Weng, J, Travis, GH

Proc. Natl. Acad. Sci. U.S.A. 2000
9843937 Isolation and one-step preparation of A2E and iso-A2E, fluorophores from human retinal pigment epithelium

Parish, CA, Hashimoto, M, Nakanishi, K, Dillon, J, Sparrow, J

Proc. Natl. Acad. Sci. U.S.A. 1998
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