Synthesis and conformational analysis of linear homo- and heterooligomers from novel 2-C-branched sugar amino acids (SAAs)

Tian, Guangzong; Hu, Jing; Zhang, Hengxi; Rademacher, Christoph; Zou, Xiang; Zheng, Hongning; Fei, Xu; Wang, Xiaoli; Linker, Torsten; Yin, Jian

doi:10.1038/s41598-018-24927-6

Cited by 6 publications

(5 citation statements)

References 64 publications

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“…A transition-metal-mediated radical reaction led to well-defined carbopeptoids with different lengths . Circular dichroism revealed that these structures adopt well-extended left- or right-handed conformations, depending on the size of the chain.…”

Section: Toward Sugar Foldamersmentioning

confidence: 99%

“…Despite the quite straightforward synthesis, − carbopeptoids have not yet been extensively exploited as structural building blocks. In contrast, peptides with defined secondary structures as well as unnatural foldamers have raised considerable attention in biology and materials science. ,, We believe that a similar approach applied to carbopeptoids could fuel the formation of novel materials.…”

Section: Toward Sugar Foldamersmentioning

confidence: 99%

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Structural Studies Using Unnatural Oligosaccharides: Toward Sugar Foldamers

et al. 2019

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Biopolymers, like DNA and proteins, fold in specific conformations in order to exert complex biological functions. Synthetic modifications are commonly used to alter those conformations and create engineered biomaterials. In stark contrast, the chemical complexity and dynamic nature of polysaccharides have hampered a detailed structural characterization and structure−function correlations are still incomplete. Many synthetic strategies have been developed to access complex unnatural oligosaccharides, capable of mimicking or even improving the properties of the natural counterpart. However, the structural features behind these results are often neglected. This perspective highlights the approaches adopted to develop unnatural glycans, with a particular focus on how the insertion of specific modifications results in more flexible or more constrained structures. Synthetic analogues of natural oligosaccharides could shine light on fundamental structural features. The combination of modern synthetic, computational, and analytical methods will result in novel carbohydrate based foldamers, with defined shape and aggregation behavior. Multiple applications in biology, material science, and nanotechnology can be envisioned.

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Section: Toward Sugar Foldamersmentioning

confidence: 99%

Section: Toward Sugar Foldamersmentioning

confidence: 99%

Structural Studies Using Unnatural Oligosaccharides: Toward Sugar Foldamers

et al. 2019

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“…A coupling of monosaccharide amine 11 and acid 12 using diphenylphosphoryl azide (DPPA) and triethylamine (Et 3 N) gave amide‐coupled compound 13 in 91% yield. [ 16 ] Subsequent oxidative cleavage of the 2‐naphthylmethyl (Nap) group using 2,3‐dichloro‐5,6‐dicyano‐1,4‐benzoquinone (DDQ) afforded the desired linker‐appended acceptor 7 in 70% yield.…”

Section: Resultsmentioning

confidence: 99%

Chemical Synthesis of a Key Precursor Relevant to the Tetrasaccharide Repeating Unit from Treponema mediumATCC 700293

Sun,

Tian,

Ding

et al. 2024

Chin. J. Chem.

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Comprehensive SummaryTreponema is a Gram‐negative anaerobic bacterium, among which the pathogenic Treponema can cause various diseases, such as venereal syphilis (Treponema pallidum), yaws (Treponema carateum), and oral diseases (Treponema denticola and Treponema medium). Although different from conventional lipopolysaccharides, the extracellular glycoconjugate of Treponema may still be a potential antigen and provide a candidate for vaccine development. Hence, we completed the first chemical synthesis of Treponema medium ATCC 700293 tetrasaccharide precursor containing L‐ornithine (L‐Orn) and D‐aspartic acid (D‐Asp) derivatives. The efficiency of non‐reducing end disaccharide formation has been improved by optimizing the assembly of the protecting groups in the donors and acceptors. Our [3+1] glycosylation strategy attempted to reduce the length of the acceptor to increase the nucleophilicity of the hydroxyl group, thereby improving the efficiency of synthesizing the target tetrasaccharide. The L‐Orn derivative was introduced at the final stage due to its influence on the glycosylation stereospecificity and efficiency. Therefore, the successful introduction of two amino acid derivatives and the synthesis of a tetrasaccharide precursor with complex functional‐group modifications have provided valuable insights for synthesizing other complex bacterial glycans.

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“…In such a case, the observation of the characteristic protons arising from the adjacent carbon atoms to the N-acetyl or -NH 2 groups, along with the resonances of all the -NH-, -NH 2 protons which resonate downfield at 7.00-8.50 ppm (sharp doublets, J= 7-8 Hz) are crucial for the amino sugar moiety recognition. Protons of the amino sugars' amine groups exhibit a unique NOE correlation pattern in the NOESY NMR spectrum, revealing correlations with the polysaccharide's backbonesuch as i+1 NH -i H1, i+1 NH-i H2 -and in some cases also within the sugar ring (Tian et al, 2018). This characteristic NOESY pattern is of great importance since it is has not been described in the literature so far and it is diagnostic for the type and the composition of saccharide units of the polysaccharide/ lipopolysaccharide SAA.…”

Section: Glycolipids Saccharides Polysaccharides and Lipo-polysacchar...mentioning

confidence: 99%

Multi-method biophysical analysis in discovery, identification, and in-depth characterization of surface‐active compounds

et al. 2022

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Synthetic surfactants are used in several industries, including manufacturing, pharmaceutical and cosmetic’s, food and feed, agriculture, petroleum and environmental remediation for their ability to adsorb to fluid and solid-water interfaces. However, their widespread use and their synthetic preparation through environmentally unfavorable processes counterbalances the value of this class of reagents. This fact has stimulated new efforts to exploit natural sources of surfactants, such as new classes of bacterial systems or manipulation of existing biological systems, that may produce, through an environmentally friendly process, new biodegradable surfactants and emulsifiers of high commercial value. A downside of microbial production of biobased chemicals such as these types of chemicals, is that their fermentation often yields crude materials consisting of several bioproducts with complex physical and chemical properties. Extraction, identification, and efficient characterization of biosurfactants from a crude mixture of biomolecules requires carefully designed, and detailed analytical processes using state-of-the-art methods. The purpose of this review article is to present the current state-of-the-art and future outlook on the various multidisciplinary biophysical methods applied in the discovery, extraction identification, and in-depth characterization of microbially-produced surface‐active compounds.

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Synthesis and conformational analysis of linear homo- and heterooligomers from novel 2-C-branched sugar amino acids (SAAs)

Cited by 6 publications

References 64 publications

Structural Studies Using Unnatural Oligosaccharides: Toward Sugar Foldamers

Structural Studies Using Unnatural Oligosaccharides: Toward Sugar Foldamers

Chemical Synthesis of a Key Precursor Relevant to the Tetrasaccharide Repeating Unit from Treponema mediumATCC 700293

Multi-method biophysical analysis in discovery, identification, and in-depth characterization of surface‐active compounds

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