Toward Automated Enzymatic Synthesis of Oligosaccharides DOI
Liuqing Wen,

Garrett Edmunds,

Christopher Gibbons

et al.

Chemical Reviews, Journal Year: 2018, Volume and Issue: 118(17), P. 8151 - 8187

Published: July 16, 2018

Oligosaccharides together with oligonucleotides and oligopeptides comprise the three major classes of natural biopolymers. Automated systems for oligonucleotide oligopeptide synthesis have significantly advanced developments in biological science by allowing nonspecialists to rapidly easily access these Researchers endeavored decades develop a comparable general automated system synthesize oligosaccharides. Such would revolutionary impact on understanding roles glycans systems. The main challenge achieving is lack synthetic methods routine glycans. Currently, two homogeneous glycoconjugates are chemical enzymatic synthesis. Enzymatic glycosylation can proceed stereo- regiospecifically without protecting group manipulations. Moreover, reaction conditions enzyme-catalyzed glycosylations extremely mild when compared glycosylations. Over past few years methodology toward oligosaccharides has been developed. Conversely, while conceptually possible, it not as well goal this survey provide foundation which continued technological advancements be made promote

Language: Английский

“One-Pot” Protection, Glycosylation, and Protection–Glycosylation Strategies of Carbohydrates DOI
Suvarn S. Kulkarni, Cheng‐Chung Wang, Narayana Murthy Sabbavarapu

et al.

Chemical Reviews, Journal Year: 2018, Volume and Issue: 118(17), P. 8025 - 8104

Published: June 5, 2018

Carbohydrates, which are ubiquitously distributed throughout the three domains of life, play significant roles in a variety vital biological processes. Access to unique and homogeneous carbohydrate materials is important understand their physical properties, functions, disease-related features. It difficult isolate carbohydrates acceptable purity amounts from natural sources. Therefore, complex saccharides with well-defined structures often most conviently accessed through chemical syntheses. Two major hurdles, regioselective protection stereoselective glycosylation, faced by chemists synthesizing these highly complicated molecules. Over past few years, there has been radical change tackling problems speeding up synthesis oligosaccharides. This largely due development one-pot protection, protection-glycosylation protocols streamlined approaches orthogonally protected building blocks, including those rare sugars, that can be used glycan coupling. In addition, new automated strategies for oligosaccharide syntheses have reported not only program-controlled assembly on solid support but also stepwise glycosylation solution phase. As result, various sugar molecules complex, large could successfully synthesized. To summarize recent advances, this review describes methodologies into glycans chronological developments associated

Language: Английский

Citations

280
Uniquely human evolution of sialic acid genetics and biology DOI
Ajit Varki

Proceedings of the National Academy of Sciences, Journal Year: 2010, Volume and Issue: 107(supplement_2), P. 8939 - 8946

Published: May 5, 2010

Darwinian evolution of humans from our common ancestors with nonhuman primates involved many gene-environment interactions at the population level, and resulting human-specific genetic changes must contribute to "Human Condition." Recent data indicate that biology sialic acids (which directly involves less than 60 genes) shows more 10 uniquely human in comparison closest evolutionary relatives. Known outcomes are tissue-specific abundant cell-surface glycans, specificity and/or expression multiple proteins recognize these novel pathogen regimes. Specific events include Alu-mediated inactivation CMAH gene, loss synthesis Sia N-glycolylneuraminic acid (Neu5Gc) increase precursor N-acetylneuraminic (Neu5Ac); increased alpha2-6-linked Sias (likely because changed ST6GALI); SIGLEC genes encoding Sia-recognizing Ig-like lectins (Siglecs). The last includes binding (in Siglecs -5, -7, -9, -11, -12); pattern -1, -6, -11); gene conversion (SIGLEC11); deletion or pseudogenization (SIGLEC13, SIGLEC14, SIGLEC16). A nongenetic outcome mutation is metabolic incorporation foreign dietary Neu5Gc, face circulating anti-Neu5Gc antibodies, generating a "xeno-auto-antigen" situation. Taken together, suggest both associated related impacts environment comprise relative "hot spot" physiological evolution, implications for features health disease.

Language: Английский

Citations

262
Solving Glycosylation Disorders: Fundamental Approaches Reveal Complicated Pathways DOI Creative Commons
Hudson H. Freeze, Jessica X. Chong, Michael J. Bamshad

et al.

The American Journal of Human Genetics, Journal Year: 2014, Volume and Issue: 94(2), P. 161 - 175

Published: Feb. 1, 2014

Language: Английский

Citations

246
Altered glycosylation in cancer: A promising target for biomarkers and therapeutics DOI

Divya Thomas,

Ashok Kumar Rathinavel,

Prakash Radhakrishnan

et al.

Biochimica et Biophysica Acta (BBA) - Reviews on Cancer, Journal Year: 2020, Volume and Issue: 1875(1), P. 188464 - 188464

Published: Nov. 4, 2020

Language: Английский

Citations

241
Ultraviolet Photodissociation Mass Spectrometry for Analysis of Biological Molecules DOI
Jennifer S. Brodbelt,

Lindsay Morrison,

Inês C. Santos

et al.

Chemical Reviews, Journal Year: 2019, Volume and Issue: 120(7), P. 3328 - 3380

Published: Dec. 18, 2019

The development of new ion-activation/dissociation methods continues to be one the most active areas mass spectrometry owing broad applications tandem in identification and structural characterization molecules. This Review will showcase impact ultraviolet photodissociation (UVPD) as a frontier strategy for generating informative fragmentation patterns ions, especially biological molecules whose complicated structures, subtle modifications, large sizes often impede molecular characterization. UVPD energizes ions via absorption high-energy photons, which allows access dissociation pathways relative more conventional ion-activation methods. Applications analysis peptides, proteins, lipids, other classes biologically relevant are emphasized this Review.

Language: Английский

Citations

228
Expression system for structural and functional studies of human glycosylation enzymes DOI
Kelley W. Moremen,

Annapoorani Ramiah,

Melissa A. Stuart

et al.

Nature Chemical Biology, Journal Year: 2017, Volume and Issue: 14(2), P. 156 - 162

Published: Dec. 18, 2017

Language: Английский

Citations

222
Fast and comprehensive N- and O-glycoproteomics analysis with MSFragger-Glyco DOI
Daniel A. Polasky, Fengchao Yu, Guo Ci Teo

et al.

Nature Methods, Journal Year: 2020, Volume and Issue: 17(11), P. 1125 - 1132

Published: Oct. 5, 2020

Language: Английский

Citations

212
Targeting Glycosylation: A New Road for Cancer Drug Discovery DOI Creative Commons
Ana Filipa Costa, Diana Campos, Celso A. Reis

et al.

Trends in cancer, Journal Year: 2020, Volume and Issue: 6(9), P. 757 - 766

Published: May 4, 2020

Cancer is a deadly disease that encompasses numerous cellular modifications. Among them, alterations in glycosylation are proven reliable hallmark of cancer, with most biomarkers used the clinic detecting cancer-associated glycans. Despite their clear potential as therapy targets, glycans have been overlooked drug discovery strategies. The complexity associated process, and lack specific methodologies to study it, long hampered progress. However, recent advances new methodologies, such glycoengineering cells high-throughput screening (HTS), opened avenues discovery. We envision glycan-based targeting has start era cancer therapy. In this article, we discuss promise for effective drugs.

Language: Английский

Citations

208
Achieving Controlled Biomolecule–Biomaterial Conjugation DOI Creative Commons
Christopher D. Spicer, E. Thomas Pashuck, Molly M. Stevens

et al.

Chemical Reviews, Journal Year: 2018, Volume and Issue: 118(16), P. 7702 - 7743

Published: July 24, 2018

The conjugation of biomolecules can impart materials with the bioactivity necessary to modulate specific cell behaviors. While biological roles particular polypeptide, oligonucleotide, and glycan structures have been extensively reviewed, along influence attachment on material structure function, key role played by strategy in determining activity is often overlooked. In this review, we focus chemistry biomolecule provide a comprehensive overview strategies for achieving controlled biomaterial functionalization. No universal method exists optimal attachment, here will discuss both relative advantages disadvantages each technique. doing so, highlight importance carefully considering impact suitability technique during design.

Language: Английский

Citations

204
Chemoenzymatic Methods for the Synthesis of Glycoproteins DOI
Chao Li, Lai‐Xi Wang

Chemical Reviews, Journal Year: 2018, Volume and Issue: 118(17), P. 8359 - 8413

Published: Aug. 24, 2018

Glycosylation is one of the most prevalent posttranslational modifications that profoundly affects structure and functions proteins in a wide variety biological recognition events. However, structural complexity heterogeneity glycoproteins, usually resulting from variations glycan components and/or sites glycosylation, often complicates detailed structure–function relationship studies hampers therapeutic applications glycoproteins. To address these challenges, various chemical strategies have been developed for producing glycan-defined homogeneous This review highlights recent advances development chemoenzymatic methods synthesizing including generation glycosynthases synthetic purposes, endoglycosidase-catalyzed glycoprotein synthesis remodeling, direct enzymatic glycosylation polypeptides proteins. The scope, limitation, future directions each method are discussed.

Language: Английский

Citations

204