PMID: 9437720Jan 1, 1997Paper

Peptide biotinylation with amine-reactive esters: differential side chain reactivity

Peptides
B T MillerA Kurosky

Abstract

N-hydroxysuccinimide (NHS) esters of biotin are reported to react specifically with amino groups of peptides and proteins. However, we have found that these reagents can readily acylate other functional groups in specific peptide sequences under relatively mild conditions. We have extended our inquiry of sequence-dependent acylation by evaluating the reactivity of a variety of commonly employed biotinylation reagents typically used for amino group modification. These included the p-nitrophenyl ester of biotin, NHS-esters of biotin containing aminohexanoic acid spacer arms, and a sulfonated NHS-biotin ester that contained a disulfide bond within its spacer. The decapeptide [D-Lys6]gonadotropin releasing hormone was employed as a model peptide. Reaction products were characterized by high-performance liquid chromatography, amino acid compositional analysis, reaction with hydroxylamine, and mass spectrometry. In addition to the O-acylation of Ser4 and Tyr5 in this peptide, we have also identified a novel biotinylation of the Arg8 side chain.

References

Aug 15, 1991·Analytical Biochemistry·J S SmithA Kurosky
Jun 27, 1990·Journal of Chromatography·E A Bayer, M Wilchek
Jan 1, 1990·Methods in Enzymology·M Wilchek, E A Bayer
Oct 1, 1989·Trends in Biochemical Sciences·M Wilchek, E A Bayer
May 15, 1988·Analytical Biochemistry·M Wilchek, E A Bayer
Oct 15, 1993·Biochemical and Biophysical Research Communications·B T Miller, A Kurosky
Jan 5, 1996·Biochemical and Biophysical Research Communications·B T Miller

❮ Previous
Next ❯

Citations

Feb 11, 2003·Peptides·Diane E ChicoBrian T Miller
Nov 23, 2011·Analytical Chemistry·Chien-Wen Hung, Andreas Tholey
Jul 10, 2012·Journal of the American Chemical Society·William M McGeeScott A McLuckey
Jan 10, 2009·Journal of Mass Spectrometry : JMS·Stefanie MädlerRenato Zenobi
Sep 18, 2007·Journal of Neurochemistry·Marco I GonzálezMichael B Robinson
Feb 6, 2014·Rapid Communications in Mass Spectrometry : RCM·Ekaterina DariiJean-Claude Tabet
Aug 11, 2015·Chemical Reviews·Hakho LeeRalph Weissleder
Nov 26, 2009·Analytical Biochemistry·Stefanie MädlerRenato Zenobi
Jan 28, 2014·International Journal of Mass Spectrometry·William M McGee, Scott A McLuckey
Apr 28, 2016·Methods : a Companion to Methods in Enzymology·Martina Marchetti-DeschmannBarbara Cvak
Sep 15, 2016·Chemical Reviews·Bauke Albada, Nils Metzler-Nolte
Apr 27, 2017·ACS Chemical Biology·Carl C WardDaniel K Nomura
Sep 8, 2017·Journal of Biomedical Materials Research. Part a·Vince BeachleyJennifer Elisseeff
Aug 24, 2007·The Journal of Biological Chemistry·Marco I GonzálezMichael B Robinson
Oct 22, 2002·American Journal of Physiology. Gastrointestinal and Liver Physiology·P SinghA Owlia
Mar 19, 2019·Rapid Communications in Mass Spectrometry : RCM·Santosh A MisalJames P Reilly
Nov 16, 2007·Journal of Proteome Research·Nicolas AbelloRainer Bischoff

❮ Previous
Next ❯

Related Concepts

Trending Feeds

COVID-19

Coronaviruses encompass a large family of viruses that cause the common cold as well as more serious diseases, such as the ongoing outbreak of coronavirus disease 2019 (COVID-19; formally known as 2019-nCoV). Coronaviruses can spread from animals to humans; symptoms include fever, cough, shortness of breath, and breathing difficulties; in more severe cases, infection can lead to death. This feed covers recent research on COVID-19.

Blastomycosis

Blastomycosis fungal infections spread through inhaling Blastomyces dermatitidis spores. Discover the latest research on blastomycosis fungal infections here.

Nuclear Pore Complex in ALS/FTD

Alterations in nucleocytoplasmic transport, controlled by the nuclear pore complex, may be involved in the pathomechanism underlying multiple neurodegenerative diseases including Amyotrophic Lateral Sclerosis and Frontotemporal Dementia. Here is the latest research on the nuclear pore complex in ALS and FTD.

Applications of Molecular Barcoding

The concept of molecular barcoding is that each original DNA or RNA molecule is attached to a unique sequence barcode. Sequence reads having different barcodes represent different original molecules, while sequence reads having the same barcode are results of PCR duplication from one original molecule. Discover the latest research on molecular barcoding here.

Chronic Fatigue Syndrome

Chronic fatigue syndrome is a disease characterized by unexplained disabling fatigue; the pathology of which is incompletely understood. Discover the latest research on chronic fatigue syndrome here.

Evolution of Pluripotency

Pluripotency refers to the ability of a cell to develop into three primary germ cell layers of the embryo. This feed focuses on the mechanisms that underlie the evolution of pluripotency. Here is the latest research.

Position Effect Variegation

Position Effect Variagation occurs when a gene is inactivated due to its positioning near heterochromatic regions within a chromosome. Discover the latest research on Position Effect Variagation here.

STING Receptor Agonists

Stimulator of IFN genes (STING) are a group of transmembrane proteins that are involved in the induction of type I interferon that is important in the innate immune response. The stimulation of STING has been an active area of research in the treatment of cancer and infectious diseases. Here is the latest research on STING receptor agonists.

Microbicide

Microbicides are products that can be applied to vaginal or rectal mucosal surfaces with the goal of preventing, or at least significantly reducing, the transmission of sexually transmitted infections. Here is the latest research on microbicides.