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Synthesis Of Glycoproteins And Glycopeptide Mimetics
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Book Synopsis Glycopeptides and Glycoproteins by : Valentin Wittmann
Download or read book Glycopeptides and Glycoproteins written by Valentin Wittmann and published by Springer Science & Business Media. This book was released on 2007-02-13 with total page 271 pages. Available in PDF, EPUB and Kindle. Book excerpt: In the last 50 years molecular biology was dominated by the exploration of proteins and nucleic acids. Beside their role in energy metabolism, oligos- charides,which represent thethirdclass ofbiomacromolecules, have received less attention. Today it is well established that oligosaccharides are involved in many important biologicalregulation and recognition processes fromp- tein folding to cell-cell communication. Glycosylation of proteins is the most complexformofco-andposttranslationalmodi'cation. Thedeterminationof structure-function relationships, however, remains dif'cult due to the mic- heterogeneity of glycoproteins that exist in many different glycoforms. Thus chemical synthesis of glycoproteins and glycopeptides with de'ned glycan structures plays a pivotal role for the detailed determination of the role of protein glycosylation. This topic is covered by the ?rst two chapters of this bookdealingwiththechemicaland enzymatic synthesis ofglycopeptides and glycoproteins. The third chapter describes the construction of glycopeptide andglycoproteinmimetics containingnon-naturalstructuralelements. These so-calledneoglycopeptidesandneoglycoproteins,respectively,canprovide- sight on the importance of distinct structural elements on biological activity andmayhaveimproved propertiessuchasanincreased stability. Theappli- tion of synthetic glycopeptides, in many cases at the clinical level, as vaccines forbothcancerandHIVisthesubjectofthefourthchapter. Glycopeptide antibiotics are glycosylated secondary metabolites of bacteria and fungi that are synthesized by non-ribosomal peptide synthetases. Some of them serve as antibiotics of last resort in the treatment of nosocomial infections with enterococci and methicillin-resistant Staphylococcus aureus (MRSA) strains. Their structure, biosynthesis, and mode of action are summarized in the ?fth chapter. The last chapter covers current methods for the determination of high-resolution structures of glycopeptides and glycoproteins mainly based onNMRspectroscopy, X-raycrystallography,and molecular modeling.
Book Synopsis Synthesis of Glycoproteins and Glycopeptide Mimetics by : Lisa Ann Marcaurelle
Download or read book Synthesis of Glycoproteins and Glycopeptide Mimetics written by Lisa Ann Marcaurelle and published by . This book was released on 2001 with total page 490 pages. Available in PDF, EPUB and Kindle. Book excerpt:
Book Synopsis Chemical Biology of Glycoproteins by : Zhongping Tan
Download or read book Chemical Biology of Glycoproteins written by Zhongping Tan and published by Royal Society of Chemistry. This book was released on 2017-03-27 with total page 441 pages. Available in PDF, EPUB and Kindle. Book excerpt: Glycans play a vital role in modulating protein structure and function from involvement in protein folding, solubility and stability to regulation of tissue distribution, recognition specificity, and biological activity. They can act as both positive and negative regulators of protein function, providing an additional level of control with respect to genetic and environmental conditions. Due to the complexity of glycosylated protein forms, elucidating structural and functional information has been challenging task for researchers but recent development of chemical biology-based tools and techniques is bridging these knowledge gaps. This book provides a thorough review of the current state of glycoprotein chemical biology, describing the development and application of glycoprotein and glycan synthesis technologies for understanding and manipulating protein glycosylation.
Book Synopsis Glycopeptides and Related Compounds by : David G. Large
Download or read book Glycopeptides and Related Compounds written by David G. Large and published by CRC Press. This book was released on 1997-05-06 with total page 786 pages. Available in PDF, EPUB and Kindle. Book excerpt: "Presents state-of-the-art methods for the synthesis, analysis, and conformational investigation of glycoproteins and glycopeptides. Discusses the history of glycopeptide synthesis, therapeutic applications, and the future of research."
Book Synopsis Development of Chemical Methods for the Synthesis of Glycopeptides and Glycoproteins by : Yu-Ying Yang
Download or read book Development of Chemical Methods for the Synthesis of Glycopeptides and Glycoproteins written by Yu-Ying Yang and published by . This book was released on 2007 with total page 400 pages. Available in PDF, EPUB and Kindle. Book excerpt: Based on the same principle of native chemical ligation and auxiliary-assisted ligation, we recently developed the "sugar-assisted ligation" method for glycopeptide and glycoprotein synthesis. In this method, we take the advantage of sugar by anchoring a thiol handle onto the C2 position of sugar moiety to facilitate the transthioesterification followed by S to N acyl transfer. The sugar moiety utilizes its rigid conformation to bring the two reacting groups of thioester intermediate into close proximity to facilitate acyl transfer. The ligation junction in sugar-assisted ligation tolerates a broad spectrum of amino acids with high preference to less hindered residues (Gly, Ala) and those with side chain that can serve as a general base (His, Asp) in the ligation pathway. The utility of this ligation method has been demonstrated in the successful synthesis of [beta]-O-linked glycopeptides, N-linked glycopeptides, [alpha]-O-linked glycopeptide and "mucin-type" [alpha]-O-linked glycoproteins. Enzymatic peptide ligation using subtilisin BPN' 8397 was also exploited here for the synthesis of a-linked glycopeptides. Under the kinetically-controlled conditions, we successfully performed the enzymatic ligations where N-linked, [alpha]-O-linked or [alpha]-S-linked glycopeptides reacted as the acyl donors. In comparison with N-linked glycopeptides, [alpha]-linked glycopeptide, where the sugar moieties located at their P2 positions, showed superior enzymatic ligation efficiencies. On the other hand, to further explore the utility of expressed protein ligation method on the synthesis of glycosylated hIL-2, we continued our previous efforts here to synthesize the native hIL-2 glycoform. We utilized the highly-specific TEV protease to remove the affinity tag from recombinant His-tagged hIL-2, and unmasked the N-terminal cysteine for ligation. Various glycopeptide thioesters, which were synthesized by chemical or chemo-enzymatic methods, were ligated to truncated IL-2 fragment (residues 6-133). The ligation studies suggested that moving the sugar moiety farther away from the ligation junction is able to improve the ligation yield. Besides, in order to isolate the ligation product from other protein mixtures, we developed and tested several affinity chromatography methods to purify glycosylated human IL-2.
Book Synopsis Towards Synthesis of Glycopeptides/Glycoproteins Via Serine/Threonine Ligation by : CI Xu
Download or read book Towards Synthesis of Glycopeptides/Glycoproteins Via Serine/Threonine Ligation written by CI Xu and published by Open Dissertation Press. This book was released on 2017-01-27 with total page pages. Available in PDF, EPUB and Kindle. Book excerpt: This dissertation, "Towards synthesis of glycopeptides/glycoproteins via serine/threonine ligation" by Ci, Xu, 许辞, was obtained from The University of Hong Kong (Pokfulam, Hong Kong) and is being sold pursuant to Creative Commons: Attribution 3.0 Hong Kong License. The content of this dissertation has not been altered in any way. We have altered the formatting in order to facilitate the ease of printing and reading of the dissertation. All rights not granted by the above license are retained by the author. Abstract: Glycoproteins are proteins that are post-translationally modified with oligosaccharides. Due to the non-template-mediated biosynthesis of glycoproteins in the nature, glycoproteins always exist as heterogeneous mixtures with different glycan structures. In order to obtain the homogeneous glycoproteins with the well-defined glycan structures for an extensive investigation of the relationship between the structure and function of glycoproteins, synthetic strategies including chemical and chemoenzymatic synthesis have been employed and achieved great success over the past years. Among these approaches, our research group has developed a novel serine/threonine ligation (STL), which involved a chemoselective ligation between a peptide with a salicylaldehyde (SAL) ester at the C-terminus and an N-terminal serine or threonine of another peptide to generate the natural Xxx-Ser/Thr linkage (Xxx represents any amino acid) at the conjugation site. STL provides more possibilities for disconnection sites for convergent protein/glycoprotein synthesis. My research has been focused on the synthesis of MUC1 glycopeptides. MUC1 is a transmemberane glycoprotein expressed on the apical surface of most normal epithelial cells at low levels but highly overexpressed on the entire membrane of human epithelial tumor cells. In the extracellular part, MUC1 contains a variable number of tandem repeat (VNTR) units which consist of twenty amino acids with five potential O-glycosylation sites. As MUC1 has been shown asa promising target for the production of immunostimulating antigens, a variety of chemical assembly strategies have been applied for the development of MUC1 glycopeptide-based anticancer vaccines with high immunogenicity and tumor selectivity, including the construction of multivalent dendrimers presenting tumor-associated MUC1 glycopeptide antigens and the incorporation of various immunoadjuvants. In my studies, I have successfully synthesized the large MUC1 VNTR glycopeptides (40-mer and 80-mer sections) possessing tumor-associated Tn antigens via one and three consecutive STL reactions. On the other hand, the cyclic MUC1 glycopeptide-BSA conjugates has been successfully constructed. We are yet to test the immunological properties of synthetic MUC1 glycopeptide oligomers and MUC1-based glycoconjugates as anticancer vaccine candidates. In addition, inspired by STL, I have developed an aspartic acid ligation, in which a C-terminal peptide-SAL ester chemoselectively reacts with an N-terminal diol group of another peptide under the same conditions as STL to form a six-membered N, O-benzylidene acetal linked intermediate. Followed by treatment with acidsand selectiveoxidation, the natural Xxx-Asplinkage(Xxx represents any amino acid) is chemoselectively generated at the conjugation site. This STL-based aspartic acid ligation has been applied in the synthesis of a series of cyclic and linear peptides. Subjects: Glycopeptides - Synthesis Glycoproteins - Synthesis
Book Synopsis The Synthesis of Glycopeptides and Glycoproteins by : Karen Anne Sage
Download or read book The Synthesis of Glycopeptides and Glycoproteins written by Karen Anne Sage and published by . This book was released on 1996 with total page 458 pages. Available in PDF, EPUB and Kindle. Book excerpt:
Book Synopsis Synthesis of Glycoproteins and C-linked Glycopeptides by : Holger Kramer
Download or read book Synthesis of Glycoproteins and C-linked Glycopeptides written by Holger Kramer and published by . This book was released on 2006 with total page 426 pages. Available in PDF, EPUB and Kindle. Book excerpt:
Book Synopsis Chemoenzymatic Synthesis of Homogeneous Glycopeptides and Glycoproteins for Functional Studies by : Jared Nyabuto Orwenyo
Download or read book Chemoenzymatic Synthesis of Homogeneous Glycopeptides and Glycoproteins for Functional Studies written by Jared Nyabuto Orwenyo and published by . This book was released on 2013 with total page 354 pages. Available in PDF, EPUB and Kindle. Book excerpt: Functional and structural studies on glycoproteins are hampered by lack of homogeneous structures due to the inherent structural heterogeneity in the pendant glycans which makes separation by routine chromatographic techniques extremely difficult. To address this problem, we used a chemoenzymatic method to make homogeneous glycopeptides and glycoproteins, which relies on the glycosynthase-based transglycosylation of a GlcNAc-peptide/protein using synthetic glycan oxazoline as the enzyme substrate. The thesis research presented here consists of three projects.
Book Synopsis Synthesis of Cancer-associated Glycopeptides and Glycoproteins by : Candy Ka Yin Chun
Download or read book Synthesis of Cancer-associated Glycopeptides and Glycoproteins written by Candy Ka Yin Chun and published by . This book was released on 2010 with total page 224 pages. Available in PDF, EPUB and Kindle. Book excerpt:
Book Synopsis Development and Use of Chemical and Enzymatic Methods in Both Solution and Solid Phase for the Synthesis of Glycopeptides, Glycoproteins and Oligosaccharides by : Krista Leah Witte
Download or read book Development and Use of Chemical and Enzymatic Methods in Both Solution and Solid Phase for the Synthesis of Glycopeptides, Glycoproteins and Oligosaccharides written by Krista Leah Witte and published by . This book was released on 1998 with total page 444 pages. Available in PDF, EPUB and Kindle. Book excerpt: Presented in this thesis is work on developing an in vitro chemo-enzymatic methodology for the specific construction of glycopeptides and glycoproteins of known sequence, thus providing a route to investigate the importance of displayed oligosaccharides in cellular and molecular communication. Studies of the dependence of subtilisin stability in organic solvents on the buffer counterion are presented. The synthesis and subsequent use of the known slow-binding inhibitor Boc-Ala-Val-Phe-trifluoroketone to determine the effect organic solvents have on the hydrogen bonding in the active site of subtilisin are also discussed. The use of subtilisin in the ligation of glycopeptides is explored. A systematic study is presented in which the permissiveness of subtilisin toward the glycosyl moiety in the enzyme subsites is investigated. In addition a cleavable linker is synthesized and used which provides a direct route via solid-phase to produce a peptide ester suitable for subtilisin ligation. Using the heterogeneous glycoprotein RNase B as a model compound, several novel glycoforms were synthesized enzymatically. This was done by first removing the glycan except for the inner-most GlcNAc to give a homogeneous starting material. Then glycosyltransferases were used to build the unique N-linked glycan moiety. In addition the RNase derivative containing only a single GlcNAc could be proteolyzed at the known site to give peptide S and GlcNAc-protein S. These could be religated under thermodynamic conditions to form the full GlcNAc-RNase. The new methodology was used to incorporate a heavy metal labeled sialic acid into a new RNase glycoform. Heavy atom doping is often used to help elucidate difficult structures and presently there is very little information of the structure of glycan portions of many important glycoproteins.
Book Synopsis Synthesis of Glycopeptides as Building Blocks for Glycoproteins by : Mallesham Bejugam
Download or read book Synthesis of Glycopeptides as Building Blocks for Glycoproteins written by Mallesham Bejugam and published by . This book was released on 2005 with total page 0 pages. Available in PDF, EPUB and Kindle. Book excerpt:
Book Synopsis Preface [zu: Glycopeptides and Glycoproteins by : Valentin Wittmann
Download or read book Preface [zu: Glycopeptides and Glycoproteins written by Valentin Wittmann and published by . This book was released on 2009 with total page pages. Available in PDF, EPUB and Kindle. Book excerpt:
Book Synopsis Synthesis of Glycopeptide Thioesters for the Native Chemical Ligation of N-Glycoproteins by : Daniel Varón Silva
Download or read book Synthesis of Glycopeptide Thioesters for the Native Chemical Ligation of N-Glycoproteins written by Daniel Varón Silva and published by . This book was released on 2006 with total page 143 pages. Available in PDF, EPUB and Kindle. Book excerpt:
Book Synopsis Synthesis of Glycopeptides as Building Blocks for Glycoproteins by : Mallesham Bejugam
Download or read book Synthesis of Glycopeptides as Building Blocks for Glycoproteins written by Mallesham Bejugam and published by . This book was released on 2006 with total page pages. Available in PDF, EPUB and Kindle. Book excerpt:
Book Synopsis Concepts and Techniques in Genomics and Proteomics by : N Saraswathy
Download or read book Concepts and Techniques in Genomics and Proteomics written by N Saraswathy and published by Elsevier. This book was released on 2011-07-01 with total page 271 pages. Available in PDF, EPUB and Kindle. Book excerpt: Concepts and techniques in genomics and proteomics covers the important concepts of high-throughput modern techniques used in the genomics and proteomics field. Each technique is explained with its underlying concepts, and simple line diagrams and flow charts are included to aid understanding and memory. A summary of key points precedes each chapter within the book, followed by detailed description in the subsections. Each subsection concludes with suggested relevant original references. Provides definitions for key concepts Case studies are included to illustrate ideas Important points to remember are noted
Book Synopsis Synthesis and Characterization of Glycosides by : Marco Brito-Arias
Download or read book Synthesis and Characterization of Glycosides written by Marco Brito-Arias and published by Springer Nature. This book was released on 2022-04-22 with total page 543 pages. Available in PDF, EPUB and Kindle. Book excerpt: This third edition is a comprehensive and extended study about the best known approaches for preparing the main types of glycosides, covering the classic and more recent glycosylation reactions used for preparing simple and challenging glycosides currently used as potent antiviral and antineoplastic drugs, or fluorogenic substrates used for enzymatic detection in cell biology. Besides, this new edition provides more examples of the glycosidic methodologies followed for preparing complex glycoconjugates such as glycoproteins and glycosphingolipids and gangliosides used as adjuvants or as synthetic vaccines candidates. Also, additional mechanistic evidence is presented for better understanding of the glycosylation reaction, trying to identify the variables mainly depending on protecting and leaving groups, as well as catalyst and reaction condition which altogether directs the anomeric stereo control. A chapter on the glycoside hydrolysis is included in view of the increasing interest in the use of biomass as a natural and renewable source for obtaining important intermediates or products used in food or valuable materials. The author includes information in the characterization of glycosides section with the aim of giving additional tools for the structural assignment through NMR, X-Ray and mass spectra techniques.
