| 1. |
- Gray, Christopher J., et al.
(author)
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Advancing Solutions to the Carbohydrate Sequencing Challenge
- 2019
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In: Journal of the American Chemical Society. - : American Chemical Society (ACS). - 0002-7863 .- 1520-5126. ; 141:37, s. 14463-14479
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Research review (peer-reviewed)abstract
- Carbohydrates possess a variety of distinct features with stereochemistry playing a particularly important role in distinguishing their structure and function. Monosaccharide building blocks are defined by a high density of chiral centers. Additionally, the anomericity and regiochemistry of the glycosidic linkages carry important biological information. Any carbohydrate-sequencing method needs to be precise in determining all aspects of this stereodiversity. Recently, several advances have been made in developing fast and precise analytical techniques that have the potential to address the stereochemical complexity of carbohydrates. This perspective seeks to provide an overview of some of these emerging techniques, focusing on those that are based on NMR and MS-hybridized technologies including ion mobility spectrometry and IR spectroscopy.
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| 2. |
- Sardzik, Robert, et al.
(author)
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Chemoenzymatic Synthesis of O-Mannosylpeptides in Solution and on Solid Phase
- 2012
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In: Journal of the American Chemical Society. - : American Chemical Society (ACS). - 0002-7863 .- 1520-5126. ; 134:10, s. 4521-4524
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Journal article (peer-reviewed)abstract
- O-Mannosyl glycans are known to play an important role in regulating the function of alpha-dystroglycan (alpha-DG), as defective glycosylation is associated with various phenotypes of congenital muscular dystrophy. Despite the well-established biological significance of these glycans, questions regarding their precise molecular function remain unanswered. Further biological investigation will require synthetic methods for the generation of pure samples of homogeneous glycopeptides with diverse sequences. Here we describe the first total syntheses of glycopeptides containing the tetrasaccharide NeuNAc alpha 2-3Gal beta 1-4GlcNAc beta 1-2Man alpha, which is reported to be the most abundant O-mannosyl glycan on alpha-DG. Our approach is based on biomimetic stepwise assembly from the reducing end and also gives access to the naturally occurring mono-, di-, and trisaccharide substructures. In addition to the total synthesis, we have developed a one-pot enzymatic cascade leading to the rapid synthesis of the target tetrasaccharide. Finally, solid-phase synthesis of the desired glycopeptides directly on a gold microarray platform is described.
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