Principles of modern solid-phase oligosaccharide synthesis

Bennett, Clay S.

doi:10.1039/c3ob42343c

Cited by 45 publications

(30 citation statements)

References 106 publications

(89 reference statements)

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“…Solid-phase synthesis has been optimised to obtain peptides, oligonucleotides and other molecules in an efficient fashion [232][233][234]. Everything starts from an aminoacid or nucleotide which is immobilised on a suitable solid phase (e.g., polystyrene).…”

Section: B Polypeptidesmentioning

confidence: 99%

Molecular bionics – engineering biomaterials at the molecular level using biological principles

et al. 2019

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Life and biological units are the result of the supramolecular arrangement of many different types of molecules, all of them combined with exquisite precision to achieve specific functions. Taking inspiration from the design principles of nature allows engineering more efficient and compatible biomaterials. Indeed, bionic (from bion-, unit of life and -ic, like) materials have gained increasing attention in the last decades due to their ability to mimic some of the characteristics of nature systems, such as dynamism, selectivity, or signalling. However, there are still many challenges when it comes to their interaction with the human body, which hinder their further clinical development. Here we review some of the recent progress in the field of molecular bionics with the final aim of providing with design rules to ensure their stability in biological media as well as to engineer novel functionalities which enable navigating the human body.

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Section: B Polypeptidesmentioning

confidence: 99%

Molecular bionics – engineering biomaterials at the molecular level using biological principles

et al. 2019

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“…[62][63][64] In 1999, Seeberger's research group introduced a new metathesis-based linker that they envisioned should allow the efficient, fast, and eventually automated synthesis of complex oligosaccharides. Oligosaccharide syn-thesis is much more complex and challenging than the synthesis of oligopeptides and oligonucleotides, the other two major classes of biopolymers found in living systems.…”

Section: Application Of CM To the Synthesis Of Oligosaccharidesmentioning

confidence: 99%

“…In the past two decades, lots of efforts have been made, in particular on their SP synthesis, leading to important advances in this field. [62][63][64] In 1999, Seeberger's research group introduced a new metathesis-based linker that they envisioned should allow the efficient, fast, and eventually automated synthesis of complex oligosaccharides. [65] After some model studies in solution, Merrifield resin was functionalized with an octenediol-based linker to afford 97 (Scheme 22).…”

Section: Application Of CM To the Synthesis Of Oligosaccharidesmentioning

confidence: 99%

Cross‐Metathesis on Immobilized Substrates – Application to the Generation of Synthetically and Biologically Relevant Structures

Riveira

Mata

2017

Eur J Org Chem

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Olefin metathesis constitutes a seemingly endless area of research that has had an enormous impact on several branches of chemistry, both in industry and in academia. Once the potential of this reaction as a carbon–carbon bond‐forming tool was widely recognized, its adaptation to solid‐phase chemistry naturally followed. This review documents the applications and possibilities that polymer‐bound alkenes have provided in the challenging cross‐version of olefin metathesis, through efforts that are far from exhausted.

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“…These types of assays are appealing because they are universal for all GT reactions that use nucleotide diphosphate-sugars. However, GTs are known to be incapable of complete discriminating against water as an acceptor substrate which results in donor hydrolysis [1, 2, 9, 22]. Therefore, a great care must be taken when use any of these assays for screening.…”

Section: Other Assays For Glycosyltransferasesmentioning

confidence: 99%

Glycosyltransferase engineering for carbohydrate synthesis

McArthur

Chen

2016

Biochemical Society Transactions

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Glycosyltransferases are powerful tools for the synthesis of complex and biologically important carbohydrates. Wild-type glycosyltransferases may not have all the properties and functions that are desired for large-scale production of carbohydrates that exist in nature and those with non-natural modifications. With the increasing availability of crystal structures of glycosyltransferases, especially those in the presence of donor and acceptor analogs, crystal structure-guided rational design has been quite successful in obtaining mutants with desired functionalities. With current limited understanding of the structure-activity relationship of glycosyltransferases, directed evolution continues to be a useful approach for generating additional mutants with functionality that can be screened for in a high-throughput format. Mutating the amino acid residues constituting or close to the substrate binding sites of glycosyltransferases by structure-guided directed evolution further explores the biotechnological potential of glycosyltransferases that can only be realized through enzyme engineering. This mini-review discusses the progress made towards glycosyltransferase engineering and the lessons learned for future engineering efforts and assay development.

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Principles of modern solid-phase oligosaccharide synthesis

Cited by 45 publications

References 106 publications

Molecular bionics – engineering biomaterials at the molecular level using biological principles

Molecular bionics – engineering biomaterials at the molecular level using biological principles

Cross‐Metathesis on Immobilized Substrates – Application to the Generation of Synthetically and Biologically Relevant Structures

Glycosyltransferase engineering for carbohydrate synthesis

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