Recent trends and challenges on carbohydrate-based molecular scaffolding: general consideration toward impact of carbohydrates in drug discovery and development

Mishra, Nidhi; Tiwari, Vinod; Schmidt, Richard R.

doi:10.1016/b978-0-12-816675-8.00001-4

Cited by 11 publications

(13 citation statements)

References 215 publications

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“…As the essential roles of carbohydrates in various life processes, carbohydrate-based drugs might demonstrate high specificity as novel therapeutic approaches. 21,22 So far, more than 170 commercial carbohydrate-based drugs have been successfully approved to treat various diseases (Figure 1). 23,24 For example, aminoglycosides, such as kanamycin, amikacin, containing a glucosides motif, have been widely used for the treatment of bacterial infections.…”

Section: Introductionmentioning

confidence: 99%

Enzyme-like C–H Oxidation of Glucosides Promoted by Visible Light

Jiang

Tian

et al. 2022

CCS Chem

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To match nature's prowess at using enzymes to make desired motifs in a regioselective fashion, we explore the use of visible light for the selective oxidation of the hydroxyl group to the corresponding ketosaccharide. This highly admirable approach offers several advantages over the enzymatic approach in terms of yields, the scope of substrates. Herein we report the development of a simple visible-light-promoted selective oxidation of unprotected glucosides that allows for inexpensive access to valuable ketosaccharides building blocks. The method is employed on a variety of different natural and artificial glucosides, is operationally simple and scalable, and is applied to access ketosaccharides rapidly and inexpensively.

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Section: Introductionmentioning

confidence: 99%

Enzyme-like C–H Oxidation of Glucosides Promoted by Visible Light

Jiang

Tian

et al. 2022

CCS Chem

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“…[ 13‐16 ] Synthetic carbohydrate‐based vaccines with rational well‐defined epitopes and alternative carriers are the trend of carbohydrate‐based vaccines development. [ 17‐22 ]…”

Section: Background and Originality Contentmentioning

confidence: 99%

Stereoselective Synthesis and Immunological Evaluation of Common O‐antigen of P. mirabilisOE and P. vulgarisTG103

Lai

Yang

et al. 2023

Chin. J. Chem.

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Comprehensive Summary Proteus species especially Proteus mirabilis and Proteus vulgaris are zoonotic pathogens which can cause public health disease. Owing to their antibiotic‐resistance, developing vaccines against these pathogens is urgently required. Herein, we describe the first synthesis of the common O‐antigen of Proteus mirabilis OE and Proteus vulgaris TG 103. The repeating unit incorporates two challenging 1,2‐cis‐glycosidic bonds: the 1,2‐cis‐2‐acetamido‐2‐deoxy‐glucosidic bonds were successfully constructed by use of conformation‐restrained 2‐nitroglucal donor under bifunctional organothiourea catalysis; while the 1,2‐cis‐2‐acetamido‐2‐deoxy‐galactosidic bonds were formed by use of di‐tert‐butylsilylidene protected 2‐azidogalactose donors. The synthetic fragments were screened by glycan microarray with immunized rabbit sera against purified LPS from Proteus mirabilis O54. The results revealed that the synthetic common O‐antigens both hexasaccharide 2 and nonasaccharide 3 can strongly bind with the IgG antibodies (Abs) in the sera, which is highly valuable for further immunological investigation in synthetic carbohydrate‐based vaccine development.

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“…4 Hz, H-6), 4.17 (dd, 1H, J 5′,6′a = 6.4, J 6′a,6′b = 11. 3 Hz, H-6′a), 4.08 (dd, 1H, J 5′,6′b = 6.9, J 6′a,6′b = 11. 3 Hz, H-6′b), 3.88 (td, J 4′,5′ = 1.2, J 5′,6á = J 5′,6′b ≈ 6.…”

Section: Synthesis Of Benzyl 6-o-acetyl-3-deoxy-4-s-(2346-tetra-oacet...mentioning

confidence: 99%

“…Carbohydrate derivatives are being used to treat bacterial and viral infections, cancer and diabetes. 3 A major disadvantage of using native carbohydrates as therapeutic agents lies in the inherent weak binding affinity and poor pharmacokinetic properties, drawbacks that could be overcome by the use of glycomimetics. These molecules, which mimic the structure and function of native carbohydrates, showed increased metabolic or biological stability compared to their natural counterparts.…”

Section: Introductionmentioning

confidence: 99%