Photogenerated reagents for membrane labeling. 1. Phenylnitrene formed within the lipid bilayer - PubMed

Photogenerated reagents for membrane labeling. 1. Phenylnitrene formed within the lipid bilayer

H Bayley et al. Biochemistry. 1978.

Abstract

Phenylnitrene generated photochemically from phenyl azide that is bound to artificial phospholipid vesicles labels the fatty acid chains of the lipids in low yield. The labeling yield varies from approximately 3.3% with soybean lecithin (which is highly unsaturated) to approximately 0.25% with dimyristoyllecithin (which is completely saturated). Labeling is largely eliminated by reduced glutathione in the aqueous phase. Nitrenes are evidently unsatisfactory reagents for the labeling either of lipids or by analogy of the hydrophobic portions of membrane proteins. This is mainly because the long lifetimes and electrophilic character of nitrenes will lead to the preferential labeling of extrinsic membrane components. Phenyl azide itself is further compromised as a lipophilic reagent by its rather low partition coefficient into lipid bilayers, as measured by equilibrium dialysis.

Similar articles

• Photogenerated reagents for membrane labeling. 2. Phenylcarbene and adamantylidene formed within the lipid bilayer.

  Bayley H, Knowles JR. Bayley H, et al. Biochemistry. 1978 Jun 13;17(12):2420-3. doi: 10.1021/bi00605a026. Biochemistry. 1978. PMID: 678520

• Use of lipophilic photoactivatable reagents to identify the lipid-embedded domains of membrane proteins.

  Gitler C, Bercovici T. Gitler C, et al. Ann N Y Acad Sci. 1980;346:199-211. doi: 10.1111/j.1749-6632.1980.tb22100.x. Ann N Y Acad Sci. 1980. PMID: 6930182 No abstract available.

• Photoreactive labeling of M13 coat protein in model membranes by use of a glycolipid probe.

  Hu VW, Wisnieski BJ. Hu VW, et al. Proc Natl Acad Sci U S A. 1979 Nov;76(11):5460-4. doi: 10.1073/pnas.76.11.5460. Proc Natl Acad Sci U S A. 1979. PMID: 293655 Free PMC article.

• Identifying regions of membrane proteins in contact with phospholipid head groups: covalent attachment of a new class of aldehyde lipid labels to cytochrome c oxidase.

  McMillen DA, Volwerk JJ, Ohishi J, Erion M, Keana JF, Jost PC, Griffith OH. McMillen DA, et al. Biochemistry. 1986 Jan 14;25(1):182-93. doi: 10.1021/bi00349a027. Biochemistry. 1986. PMID: 3006751

• Photochemical labeling of apolar phase of membranes.

  Brunner J. Brunner J. Methods Enzymol. 1989;172:628-87. doi: 10.1016/s0076-6879(89)72037-1. Methods Enzymol. 1989. PMID: 2664431 Review. No abstract available.

Cited by

• A photochemical approach to the lipid accessibility of engineered cysteinyl residues.

  Li J, Shi L, Karlin A. Li J, et al. Proc Natl Acad Sci U S A. 2003 Feb 4;100(3):886-91. doi: 10.1073/pnas.0237311100. Epub 2003 Jan 17. Proc Natl Acad Sci U S A. 2003. PMID: 12533666 Free PMC article.

• Engineered protein coatings to improve the osseointegration of dental and orthopaedic implants.

  Raphel J, Karlsson J, Galli S, Wennerberg A, Lindsay C, Haugh MG, Pajarinen J, Goodman SB, Jimbo R, Andersson M, Heilshorn SC. Raphel J, et al. Biomaterials. 2016 Mar;83:269-82. doi: 10.1016/j.biomaterials.2015.12.030. Epub 2016 Jan 6. Biomaterials. 2016. PMID: 26790146 Free PMC article.

• Protein-protein interactions within paramyxoviruses identified by native disulfide bonding or reversible chemical cross-linking.

  Markwell MA, Fox CF. Markwell MA, et al. J Virol. 1980 Jan;33(1):152-66. doi: 10.1128/JVI.33.1.152-166.1980. J Virol. 1980. PMID: 6245225 Free PMC article.

Publication types

MeSH terms

Substances