Photolabile Protecting <scp>Group‐Mediated</scp> Synthesis of <scp>2‐Deoxy‐Glycosides</scp>

Li, Xiaoqian; Ma, Zhi; Liu, Rongkun; Hurevich, Mattan; Yang, You

doi:10.1002/cjoc.202100477

Cited by 18 publications

(4 citation statements)

References 36 publications

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“…It was possibly due to the chirality of the thiol-protecting group of 1 , and this phenomenon would disappear after deprotection. The crude peptide 3 was dissolved in 10% acetonitrile aqueous solution, followed by irradiation at 365 nm for 5 min to remove the photocleavable protecting group 14 to give the target peptide 4 . RP-HPLC monitoring showed 4 as a single peak and ESI-MS analysis verified its molecular weight (Fig.…”

Section: Resultsmentioning

confidence: 99%

Synthesis of disulfide-rich C-terminal Cys-containing peptide acids through a photocleavable side-chain anchoring strategy

Luo,

Gao,

Zhao

et al. 2023

Org. Biomol. Chem.

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Section: Resultsmentioning

confidence: 99%

Synthesis of disulfide-rich C-terminal Cys-containing peptide acids through a photocleavable side-chain anchoring strategy

Luo,

Gao,

Zhao

et al. 2023

Org. Biomol. Chem.

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“…For oligosaccharide preparation, chemical synthesis has become an efficient and powerful approach in the past two decades. [ 31‐38 ] As a part of our ongoing research project on the development of GBS oligosaccharide‐protein conjugate vaccines, [ 39 ] we presented here the convergent synthesis of an octasaccharide derivative 1 of GBC oligosaccharide unit II, which contained the aforementioned three dominant oligosaccharide epitopes in structure. The target molecule 1 was designed to equip with an aminoethylphosphate group at C‐6 position of glucitol residue, which would enable its regioselective conjugation with biomolecules for biological and immunological studies.…”

Section: Background and Originality Contentmentioning

confidence: 99%

Chemical Synthesis of an Octasaccharide Derivative Related to Group B StreptococcusCell‐Wall Polysaccharide

et al. 2022

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Comprehensive Summary Group B Streptococcus (GBS) is the major pathogen that causes invasive infectious diseases in neonates and infants. The development of preventive and therapeutic strategies against GBS infection has been becoming the most pressing subject worldwide. Group B carbohydrate (GBC), the group B‐specific polysaccharide that distinguishes GBS with other streptococci species, has been identified as an attractive antigen for diagnosis and vaccine development because of its highly conservative tetra‐antennary structure. In this paper, a highly convergent [3 + 5] glycosylation strategy for efficient synthesis of an octasaccharide derivative related to GBC oligosaccharide unit II has been developed. In this synthesis, each glycosylation reaction was efficiently constructed with glycosyl imidates, especially trifluoroacetimidate, as donors, and each glycosidic bond was stereoselectively controlled via the neighboring group participation effect of acyl group on the 2‐O‐position of imidate donors or the solvent effect of Et2O. Furthermore, the aminoethylphosphate group was smoothly installed on the 6‐O‐position of d‐glucitol residue using the phosphoramidite method. After global deprotection, the target octasaccharide was successfully obtained from d‐glucitol in 29 steps with an overall yield of 1.37%. The free amino group installed on the aminoethylphosphate spacer of the target molecule enables its modification with functionalized biomolecules for further biological studies.

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“…o -Nitrobenzylic derivatives have been widely used for spatial and temporal mask of various chemicals . Recently, they have increasingly aroused a great deal of attention in oligosaccharide synthesis . Recognizing this, we herein report photosensitive fluorous tag II used for saccharide synthesis.…”

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confidence: 98%

Photosensitive Fluorous Tag-Assisted Convergent Synthesis of β-1,4-Mannuronates

et al. 2023

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Rapid synthesis of saccharides by a chemical method is an efficient way to meet the demand for well-defined glycans to probe their biological functions. Herein, a feasible and convenient strategy for saccharide synthesis was established by introducing a photosensitive fluorous tag at the anomeric position of glycosides. The tag was used not only in polytetrafluoroethylene-assisted rapid purification but also as a temporary protecting group at the reducing end of carbohydrates. The tag-protected glycosides could be transformed into new glycosyl donors for convergent synthesis after orthogonal deprotection of the tag by photolysis. Via combination of the β-directing C-5 carboxylate glycosylation strategy, β-1,4-mannuronates were efficiently prepared.

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Photolabile Protecting Group‐Mediated Synthesis of 2‐Deoxy‐Glycosides

Cited by 18 publications

References 36 publications

Synthesis of disulfide-rich C-terminal Cys-containing peptide acids through a photocleavable side-chain anchoring strategy

Synthesis of disulfide-rich C-terminal Cys-containing peptide acids through a photocleavable side-chain anchoring strategy

Chemical Synthesis of an Octasaccharide Derivative Related to Group B StreptococcusCell‐Wall Polysaccharide

Photosensitive Fluorous Tag-Assisted Convergent Synthesis of β-1,4-Mannuronates

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