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Unnatural Amino Acid Incorporation and Click Chemistry

Author:

Publisher: GRIN Verlag

Published: 2018-03-19

Total Pages: 53

ISBN-13: 3668663467

Seminar paper from the year 2014 in the subject Chemistry - Bio-chemistry, grade: 1,0, LMU Munich (Chemie), language: English, abstract: In the present work a modified version of yellow fluorescent protein containing an unnatural structural homologue of the natural amino acid pyrrolysine with a norbornene moiety was produced by expression in Escherichia coli. The incorporation of the unnatural amino acid was achieved by amber stop codon suppression method. A bio-othogonal click reaction was performed, binding a synthetic fluorescent dye to the modified protein. All steps towards necessary for obtaining the genetically modified organism were performed and documented. The artificial amino acid, as well as the dye used in the click reaction were synthetically prepared. The success of the project was demonstrated by LC/MS studies of the products. Fluorescence spectroscopy of click reaction product and the protein was performed, but no conclusive proof of FRET effects could as yet be made. This point remains of interest for future studies.

Non-Natural Amino Acids

Author:

Publisher: Academic Press

Published: 2009-07-24

Total Pages: 334

ISBN-13: 0080921639

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By combining the tools of organic chemistry with those of physical biochemistry and cell biology, Non-Natural Amino Acids aims to provide fundamental insights into how proteins work within the context of complex biological systems of biomedical interest. The critically acclaimed laboratory standard for 40 years, Methods in Enzymology is one of the most highly respected publications in the field of biochemistry. Since 1955, each volume has been eagerly awaited, frequently consulted, and praised by researchers and reviewers alike. With more than 400 volumes published, each Methods in Enzymology volume presents material that is relevant in today's labs -- truly an essential publication for researchers in all fields of life sciences. Demonstrates how the tools and principles of chemistry combined with the molecules and processes of living cells can be combined to create molecules with new properties and functions found neither in nature nor in the test tube Presents new insights into the molecular mechanisms of complex biological and chemical systems that can be gained by studying the structure and function of non-natural molecules Provides a "one-stop shop" for tried and tested essential techniques, eliminating the need to wade through untested or unreliable methods

Synthesis of a Novel Unnatural Amino Acid for Protein Incorporation and Click Mediated Conjugation

Author: Christopher A. Farley

Publisher:

Published: 2014

Total Pages:

ISBN-13:

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Unnatural amino acids (UAAs) contain side chains, or R groups, that are not found in the 20 canonical amino acids. These noncanonical groups afford the capability to incorporate powerful chemical capabilities in proteins that are ordinarily unavailable with the naturally-occurring amino acids. Among the most useful moieties to incorporate into proteins are functional groups that can undergo Huisgen [3+2] cycloadditions, or “click,” reactions. This reaction occurs between azides and alkynes, and its mild conditions and high regioselectivity and reactivity make it an ideal process for bioconjugation. Photoreactivity is another useful characteristic that can be conferred to UAAs. Photolabile caging groups can inhibit the function of a protein until brief irradiation with UV light induces an intramolecular rearrangement and its displacement, reestablishing normal function. In this thesis, we propose a synthesis to incorporate both of these moieties into a single UAA.

Unnatural Amino Acids Designed for Click Chemistry and Their Application to the Modification of Peptides & Nitrene Transfer Reactions Catalyzed by Metalloporphyrins

Author:

Publisher:

Published: 2009

Total Pages: 223

ISBN-13:

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The field of peptidomimetics has rapidly grown into an area of great interest for the design and synthesis of pharmaceutical drug targets. The large array of natural peptides with biological function as well as the growing understanding of the roles of these peptides in biological events has led to a large interest in these compounds as drug candidates. The majority of peptide and peptide-like molecules have not found widespread pharmaceutical utility; however, due to there lability in biological systems. This major drawback leads to the necessity for the development of peptide-like molecules with increased stability under biological conditions. To this end there has been an increased interest in the development of unnatural amino acids for the synthetic modification of peptides and proteins. Presented in this dissertation is the synthesis of a series of unnatural amino acids designed for applications to [3+2] click cycloaddition reactions. It also covers the introduction of these amino acids into the sequence of peptides for the purpose of labeling the peptide with aryl triazole chromophores in an attempt to analyze the electron transfer capabilities of aryl triazoles. The information from the fluorescent studies of these peptides will provide a basis for the design of fluorophoric peptide probes that can be introduced into a peptide at any time under labile conditions. This methodology provides a powerful tool for the analysis of peptide structure and the analysis of peptide-macromolecular interactions.

Rab GTPases and Membrane Trafficking

Author: Guangpu Li

Publisher: Bentham Science Publishers

Published: 2012-05-21

Total Pages: 180

ISBN-13: 1608053652

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"Ypt/Rab GTPases form the largest branch of the Ras-related small GTPase superfamily and regulate intracellular membrane trafficking in all eukaryotes. Since their discovery over two decades ago, a wealth of information has accumulated about the roles that"

Fluorine-containing Amino Acids

Author: Valery P. Kukhar

Publisher: John Wiley & Sons

Published: 1995-04-06

Total Pages: 432

ISBN-13:

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In recent years, organo-fluorine chemistry has made a marked impact on the design and synthesis of a large variety of biologically active molecules, such as steroids, carbohydrates, amines, amino acids, peptides and other natural products. Naturally occurring amino acids play a pivotal role in living systems, and therefore synthetic fluorine-containing amino acids have been of significant interest to researchers working towards the understanding and modification of physiological processes. Fluorine-containing Amino Acids: is the first volume devoted to the synthesis and properties of fluorine-containing amino acids pays special attention to the preparation of enantiomerically pure acids (which are essential to the modern pharmaceutical industry) deals with a rapidly expanding field of research has been written by experienced researchers who are responsible for many developments in the field highlights the interdisciplinary nature of this topic Fluorine-containing Amino Acids is the only dedicated reference in this subject and will be essential for researchers in synthetic organic, peptide, natural product, and medicinal chemistry and biochemistry.

Peptide, Protein and Enzyme Design

Author:

Publisher: Academic Press

Published: 2016-08-27

Total Pages: 686

ISBN-13: 0128054344

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De Novo Enzyme Design, the newest volume in the Methods in Enzymology series, continues the legacy of this premier serial with quality chapters authored by leaders in the field. This volume includes the design of metal binding maquettes, insertion of non-natural cofactors, Cu metallopeptides, non-covalent interactions in peptide assemblies, peptide binding and bundling, heteronuclear metalloenzymes, florinated peptides, De Novo imaging agents, and protein-protein interaction. Continues the legacy of this premier serial with quality chapters on de novo enzyme design Represents the newest volume in the Methods in Enzymology series, providing premier, quality chapters authored by leaders in the field Ideal reference for those interested in the study of enzyme design that looks at both structure and mechanism

Unnatural Amino Acids

Author: Loredano Pollegioni

Publisher: Humana Press

Published: 2011-10-05

Total Pages: 409

ISBN-13: 9781617793301

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Even though they are present in nature, non-proteinogenic amino acids are usually defined as unnatural or non-natural. Beside their structural diversity, interest in these compounds is due to their occurrence in nature, their biological properties, the analytical aspects, their use as probes, and their incorporation into peptides and proteins, among other reasons. Divided into five convenient sections, Unnatural Amino Acids: Methods and Protocols deals with enzymatic methods used to produce non-natural amino acids, aspects concerning the presence of unnatural amino acids in peptides with antimicrobial properties, genetic incorporation of unnatural amino acids into proteins (yeast and mammalian cells), and detection and quantification of D-amino acids and related enzymes. Written in the highly successful Methods in Molecular BiologyTM series format, chapters contain introductions to their respective topics, lists of the necessary materials and reagents, step-by-step, readily reproducible laboratory protocols, and notes on troubleshooting and avoiding known pitfalls. Authoritative and accessible, Unnatural Amino Acids: Methods and Protocols serves as an ideal guide for scientists and contributes to directing the attention of researchers to the many fields of growing scientific interest in non-natural amino acids.

A General Strategy for Site-specific Incorporation of Unnatural Amino Acids Into Proteins

Author: Spencer Jay Anthony-Cahill

Publisher:

Published: 1990

Total Pages: 676

ISBN-13:

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Micro and Nanofabrication Using Self-Assembled Biological Nanostructures

Author: Jaime Castillo-León

Publisher: William Andrew

Published: 2014-09-10

Total Pages: 0

ISBN-13: 9780323296427

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Self-assembled nanostructures based on peptides and proteins have been investigated and presented as biomaterials with an impressive potential for a broad range of applications such as microfabrication, biosensing platforms, drug delivery systems, bioelectronics and tissue reparation. Through self-assembly peptides can give rise to a range of well-defined nanostructures such as nanotubes, nanofibers, nanoparticles, nanotapes, gels and nanorods. However, there are challenges when trying to integrate these biological nanostructures in the development of sensing devices or drug-delivery systems - challenges such as controlling the size during synthesis, the stability in liquid environments and manipulation. In "Micro and Nanofabrication Using Self-assembled Biological Nanostructures" the options and challenges when using self-assembled peptide nanostructures in micro and nanofabrication are discussed. The publication covers different ways to manipulate, deposit and immobilize on specific locations these biological nanostructures in order to use them in the fabrication of new structures or as part of biosensing platforms. Examples where researchers used biological nanostructures for those types of applications are provided. Finally, future applications are discussed as well as parameters to accelerate and expand the use of these biological building blocks in nano- and micro-fabrication processes by taking advantage of their impressive properties such as low-cost and short synthesis time.