Controlling orientations of immobilized oligopeptides using N-terminal cysteine labels

Langmuir : the ACS Journal of Surfaces and Colloids
Xinyan BiKun-Lin Yang

Abstract

This letter reports a strategy of using N-terminal cysteine labels for controlling the immobilization of oligopeptides on aldehyde-terminated surfaces through the formation of stable thiazolidine rings. We also study the effect of cysteine position (either N-terminal or C-terminal) and lysine residue on the immobilization of oligopeptides. On the basis of our ellipsometry and quartz crystal microbalance (QCM) results, we conclude that the proposed immobilization strategy is highly site-specific. It works only when cysteine is in the N-terminal position, and the formation of thiazolidine is much faster than the formation of imines between lysine residues and aldehydes, even in the presence of a reducing agent such as NaBH(3)CN. By labeling an oligopeptide CSNKTRIDEANNKATKML with an N-terminal cysteine, we immobilize this oligopeptide on an aldehyde-terminated surface and investigate the enzymatic activity of trypsin acting on the oligopeptide. It is found that trypsin is able to cleave the immobilized oligopeptide having a single anchoring point at the N-terminal cysteine. No cleavage is observed when the oligopeptide is immobilized through multiple anchoring points at lysine residues.

References

Jan 1, 1995·International Journal of Peptide and Protein Research·J C Spetzler, J P Tam
Jul 5, 1994·Proceedings of the National Academy of Sciences of the United States of America·C F Liu, J P Tam
Jan 9, 1999·Trends in Biotechnology·G A Lemieux, C R Bertozzi
Nov 4, 2000·Nature Genetics·H ZhuM Snyder
Mar 5, 2002·Nature Biotechnology·Benjamin T HousemanMilan Mrksich
Jul 20, 2002·Bioorganic & Medicinal Chemistry Letters·Marie Laure LesaicherreShao Q Yao
Jul 20, 2002·Bioorganic & Medicinal Chemistry Letters·Marie Laure LesaicherreShao Q Yao
Sep 25, 2003·Journal of the American Chemical Society·Matthew B SoellnerRonald T Raines
Nov 5, 2003·Proteomics·Seung-yong Seong, Cheol-young Choi
Jul 22, 2004·Journal of the American Chemical Society·Yan-Yeung LukNicholas L Abbott
Dec 29, 2004·Langmuir : the ACS Journal of Surfaces and Colloids·Dora Peelen, Lloyd M Smith
Feb 1, 2005·Analytical Chemistry·Zhihong ShenXiangqun Zeng
Jul 6, 2006·Journal of the American Chemical Society·Matthew B SoellnerRonald T Raines

❮ Previous
Next ❯

Citations

May 16, 2009·Biosensors & Bioelectronics·Xinyan BiKun-Lin Yang
Jul 19, 2014·Colloids and Surfaces. B, Biointerfaces·Lian Hao OngKun-Lin Yang
Dec 17, 2009·Biomacromolecules·Yuquan ZouJayachandran N Kizhakkedathu

❮ 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.