Dimethylformamide-Modulated Kdo Glycosylation for Stereoselective Synthesis of α-Kdo Glycosides

Lou, Qixin; Hua, Qingting; Zhang, Liangliang; Yang, You

doi:10.1021/acs.orglett.9b04509

Cited by 18 publications

(13 citation statements)

References 62 publications

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“…N ‐formylpiperidine (NFP), N ‐formylmorpholine (NFM), and N , N ‐diacetylmethylamine (DAMA) were also explored for this glycosidation (entries 5—8). [ 27‐28 ] Among them, we found that glycosidation using DMF (4 equiv) as additive afforded 6a in excellent yield and better α‐selectivity (94%, α/β = 2.7 : 1; entry 8). Employment of 8 or 12 equiv of DMF for the glycosidation did not further enhance the α‐selectivity (α/β = 2.4 : 1; entries 9 and 10).…”

Section: Resultsmentioning

confidence: 99%

“…methane gave compound 10 in 72% yield, which was subjected to HF·pyridine in THF to produce o NBC‐protected sugar alcohol 11 in 76% yield after silica gel flash column chromatography. [ 28a ] Gratifyingly, the DMF (4 equiv)‐modulated SPhosAuNTf 2 (0.6 equiv)‐ promoted glycosidation of per‐ o NBC‐protected 2‐deoxy‐glucosyl ynenoate 4 with o NBC‐protected sugar alcohol 11 at 0 °C resulted in a very clean reaction, providing disaccharide 12 in an excellent 97% yield with moderate α‐selectivity (α/β = 3.6 : 1). In addition, coupling of ynenoate 4 with the disaccharide acceptor 13 [ 24c ] under the similar activation conditions was also performed (Scheme 4b).…”

Section: Resultsmentioning

confidence: 99%

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

Liu

et al. 2021

Chin. J. Chem.

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Main observation and conclusion A green and efficient photolabile protecting group (PPG)‐mediated glycosidation approach for the synthesis of 2‐deoxy‐glycosides is reported. By employing ortho‐nitrobenzyl carbonate (oNBC) as PPG, N,N‐dimethylformamide (DMF)‐modulated SPhosAuNTf2‐promoted glycosidation with per‐oNBC‐protected 2‐deoxy‐glycosyl ynenoates affords the 2‐deoxy‐glycosides with moderate to excellent α‐selectivities presumably depending on the reactivities of the acceptor alcohols. Based on the PPG‐mediated glycosidation approach, oligosaccharides with three to six oNBC groups are effectively achieved. The multiple oNBC groups in the 2‐deoxy‐glycosides are completely cleaved by irradiation at 365 nm, resulting in the desired 2‐deoxy‐glycosides in an efficient manner without affecting the common alkyne, alkene, azide functional groups and the traditional protecting groups on the aglycones.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

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

Liu

et al. 2021

Chin. J. Chem.

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“…35 DMF also inhibits cisplatin-related kidney injury by stimulating the Nrf2 pathway and repressing the NF-κB pathway. 36 DMF affects Kdo glycosylation by stereoselective synthesis for α-Kdo glycosides, 37 and regulates standard conversion potentials for oxygen and carbon dioxide couples. 38 In this study, we found that DMF inhibits high glucose-induced susceptibility to osteoporosis in vivo and suppresses high glucose-induced osteoclast differentiation in vitro .…”

Section: Discussionmentioning

confidence: 99%

N,N-Dimethylformamide inhibits high glucose-induced osteoporosis via attenuating MAPK and NF-κB signalling

Liu

2022

Bone & Joint Research

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Aims The role of N,N-dimethylformamide (DMF) in diabetes-induced osteoporosis (DM-OS) progression remains unclear. Here, we aimed to explore the effect of DMF on DM-OS development. Methods Diabetic models of mice, RAW 264.7 cells, and bone marrow macrophages (BMMs) were established by streptozotocin stimulation, high glucose treatment, and receptor activator of nuclear factor-κB ligand (RANKL) treatment, respectively. The effects of DMF on DM-OS development in these models were examined by micro-CT analysis, haematoxylin and eosin (H&E) staining, osteoclast differentiation of RAW 264.7 cells and BMMs, H&E and tartrate-resistant acid phosphatase (TRAP) staining, enzyme-linked immunosorbent assay (ELISA) of TRAP5b and c-terminal telopeptides of type 1 (CTX1) analyses, reactive oxygen species (ROS) analysis, quantitative reverse transcription polymerase chain reaction (qRT-PCR), Cell Counting Kit-8 (CCK-8) assay, and Western blot. Results The established diabetic mice were more sensitive to ovariectomy (OVX)-induced osteoporosis, and DMF treatment inhibited the sensitivity. OVX-treated diabetic mice exhibited higher TRAP5b and c-terminal telopeptides of type 1 (CTX1) levels, and DMF treatment inhibited the enhancement. DMF reduced RAW 264.7 cell viability. Glucose treatment enhanced the levels of TRAP5b, cathepsin K, Atp6v0d2, and H+-ATPase, ROS, while DMF reversed this phenotype. The glucose-increased protein levels were inhibited by DMF in cells treated with RANKL. The expression levels of antioxidant enzymes Gclc, Gclm, Ho-1, and Nqo1 were upregulated by DMF. DMF attenuated high glucose-caused osteoclast differentiation by targeting mitogen-activated protein kinase (MAPK) and nuclear factor kappa B (NF-κB) signalling in BMMs. Conclusion DMF inhibits high glucose-induced osteoporosis by targeting MAPK and NF-κB signalling. Cite this article: Bone Joint Res 2022;11(4):200–209.

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“…Lou et al. used a similar strategy for the synthesis of α‐Kdo glycosides [24] . According to this report, Lou et al.…”

Section: Synthesis Of α‐Kdo Glycosidesmentioning

confidence: 99%

Kdo Glycosylations and Their Application in Oligosaccharide Synthesis**

Pradhan¹

2023

Eur J Org Chem

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Higher carbon saccharide 3‐deoxy‐d‐manno‐oct‐2‐ulosonic acid (Kdo) is a structural unit of bacterial lipopolysaccharides (LPSs) and capsular polysaccharides (CPSs). Kdo is present in the inner core region of LPSs, and this region is structurally conserved. Being non‐mammalian in origin, Kdos are effectively recognized by the native and adaptive immune systems. Therefore, the synthesis of new Kdo derivatives and neoglycoconjugates is highly important for the development of vaccines. This review highlights recent accomplishments related to α‐glycosylations, β‐glycosylations and C‐glycosylations of Kdos and their application to the stereoselective synthesis of inner core oligosaccharides.

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Dimethylformamide-Modulated Kdo Glycosylation for Stereoselective Synthesis of α-Kdo Glycosides

Cited by 18 publications

References 62 publications

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

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

N,N-Dimethylformamide inhibits high glucose-induced osteoporosis via attenuating MAPK and NF-κB signalling

Kdo Glycosylations and Their Application in Oligosaccharide Synthesis**

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