atRAL can spontaneously react with PE to form NRPE

Stable Identifier
Reaction [transition]
Homo sapiens
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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
10852960 Biosynthesis of a major lipofuscin fluorophore in mice and humans with ABCR-mediated retinal and macular degeneration

Travis, GH, Weng, J, Mata, NL

Proc. Natl. Acad. Sci. U.S.A. 2000
5763079 Lipid to protein chromophore transfer in the photolysis of visual pigments

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

Nature 1969
9843937 Isolation and one-step preparation of A2E and iso-A2E, fluorophores from human retinal pigment epithelium

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

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