An improved strategy for the stereoselective synthesis of glycosides using glycosidases as catalysts

Baker, Anne; Turner, Nicholas J.; Webberley, Matthew C.

doi:10.1016/s0957-4166(00)80398-5

Cited by 15 publications

(4 citation statements)

References 11 publications

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“…For example, using β-glucosidase with racemic AcNH-Ser-OMe (93) as the acceptor and β-Glc-OPho-NO 2 (94) as the donor, the obtained glucoside 95 was shown to have a de of 80%. 155 After β-galactosidase-mediated glycosidation, the desired glycopeptide fragment 96 was obtained (Scheme 31).…”

Section: Glycosidases and Transglycosidasesmentioning

confidence: 99%

Recent Advances in the Chemoenzymatic Synthesis of Carbohydrates and Carbohydrate Mimetics

et al. 1996

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ContentsI. General Introduction 443 II. Aldol Addition with Aldolases 443 1. Introduction 443 2. DHAP-Dependent Aldolases 447 2.1. General Background 447 2.2. Synthetic Applications 449 3. Pyruvate-and Phosphoenolpyruvate-Dependent Aldolases 453 3.1. N-Acetylneuraminic Acid Aldolase and NeuAc Synthetase 453 3.2. 3-Deoxy-D-manno-2-octulosonate (KDO) Aldolase and 3-Deoxy-D-manno-2-octulosonate 8-Phosphate (KDO-8-P) Synthetase 456 3.3. Other Pyruvate-and Phosphoenolpyruvate-Dependent Aldolases 457 4. 2-Deoxyribose-5-phosphate Aldolase 457 5. Glycine-Dependent Aldolases 459 III. Enzymatic Glycosidation 460 1. Glycosidases and Transglycosidases 460 2. Glycosyltransferases 462 2.1. Non-Leloir Glycosyltransferases 462 2.2. Leloir-type Glycosyltransferases 463 IV. Concluding Remarks 469 V. References 469

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Section: Glycosidases and Transglycosidasesmentioning

confidence: 99%

Recent Advances in the Chemoenzymatic Synthesis of Carbohydrates and Carbohydrate Mimetics

et al. 1996

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“…Depending on reactions conditions isolated yields were in the range 13-25% [62,63]. Glycosylated serine derivatives have been also used as acceptors for additional sugar moieties.…”

Section: Glycosidases-catalyzed Formation Of Glycosidic Bondsmentioning

confidence: 99%

Hydrolysis and Formation of Glycosidic Bonds

Monti

Riva

2012

Enzyme Catalysis in Organic Synthesis

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Carbohydrates play an important role in many biological events, such as cellular communication and physiological responses. In fact, oligosaccharides and various glycoconjugates have been shown to modulate different molecular recognition processes, including viral and bacterial pathogens recognition [1][2][3][4][5], tumor-associated cell adhesion and metastasis events [6-8], immune response [9], fertilization [10], and neuronal development [11]. This significant role, together with advances in the glycomics field and the recent developments of new synthetic methodologies, for example, the glycorandomization of biologically active natural products [12,13], makes glycoconjugates extremely attractive therapeutic targets nowadays [14][15][16][17].However, the presence of multiple functional groups and stereocenters in carbohydrates makes them challenging targets for organic chemists. Time-consuming protecting group manipulations and complex synthetic schemes are often required to suitably discriminate among hydroxyl groups with similar reactivities and/or to obtain the desired glycosidic linkage by using specifically activated donors and acceptors. Both regioselectivity and stereospecificity need to be strictly controlled and, as the number of different monosaccharide units as well as of glycan structures of interest is very large, a general methodology for oligosaccharide synthesis is still far from being reached. Moreover, despite recent progress in the solid-phase synthesis of oligosaccharides [14,16,18], an automated oligosaccharide synthesizer for all purposes is not yet commercially available and not all the common glycosidic linkages are accessible. Even the structural characterization of the saccharidic part of novel glycoconjugates from natural sources is still a demanding task -no automated sequencing techniques are fully developed, unlike the case of nucleic acids and peptides.Finally, the natural complexity of glycoconjugates is amplified by the extreme variety of aglycon structures coupled to the glycan chains, which can range from Enzyme Catalysis in Organic Synthesis, Third Edition. Edited

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“…10 O-Glycosylated amino acids are important building blocks for the synthesis of glycopeptides and other glycoconjugates. [11][12][13] Rather surprisingly, very few examples of O-glycosylated α-azido amino acids have been reported [14][15][16] and even fewer of those refer to 1,2-cis glycosidic linkages. 17 In these reports the azido functional group is often installed temporarily as a masked amine and further functionalization by means of the CuAAC reaction…”

mentioning

confidence: 99%

“…[22][23][24] Thus, the preparation of α-galactosyl glycolipid 1 was envisaged from α-galactosyl Firstly, the synthesis of L-serine α-azido glycosyl acceptors 3a-c using diazo-transfer methodologies was investigated. Hence, benzyl and methyl α-azido esters 3a 25 and 3b, 16 respectively, were prepared from their corresponding N-Boc-protected derivatives 5a 26 and 5b as shown in Scheme 1. The reactions were carried out as one-pot procedures, initiated by the acidic removal of the carbamate protecting group followed by diazotransfer reaction with either trifluoromethanesulfonyl (triflyl) azide 27,28 or imidazole-1-sulfonyl azide 6 and Cu(II) catalysis in basic medium.…”

mentioning

confidence: 99%

Glycosylated α-Azido Amino Acids: Versatile Intermediates in the Synthesis of Neoglycoconjugates

O’Flaherty

Velasco‐Torrijos

2018

Synlett

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A series of glycosylated α-azido amino acids was synthesized as precursors for neoglycoconjugates, a class of important biomolecules for drug discovery, and sensor development. The synthetically challenging 1,2-cis α-galactosylated species described herein were designed as building blocks in the synthesis of analogues of α-galactosyl ceramide, a potent immunomodulator. A benzyl-protected 1,2,3-triazolyl α-galactosyl-l-serine derivative was prepared using copper azide alkyne cycloaddition to showcase the potential of glycosylated α-azido amino acids in neoglycoconjugate design.

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An improved strategy for the stereoselective synthesis of glycosides using glycosidases as catalysts

Cited by 15 publications

References 11 publications

Recent Advances in the Chemoenzymatic Synthesis of Carbohydrates and Carbohydrate Mimetics

Recent Advances in the Chemoenzymatic Synthesis of Carbohydrates and Carbohydrate Mimetics

Hydrolysis and Formation of Glycosidic Bonds

Glycosylated α-Azido Amino Acids: Versatile Intermediates in the Synthesis of Neoglycoconjugates

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