Total synthesis of artochamins F, H, I, and J through cascade reactions

Nicolaou, K. C.; Lister, Troy; Denton, Ross M.; Gelin, Christine F.

doi:10.1016/j.tet.2008.02.108

Cited by 27 publications

(16 citation statements)

References 101 publications

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“…3,4-Bis-(tert-butyl-dimethyl-silanyloxy)-benzyl bromide was synthesized according to the method developed by Nicolaou (Supplementary Information, Scheme S2) [18]. Sodium azide (4.38 g, 0.067 mol) was added to a stirred solution of 3,4-bis-(tert-butyl-dimethyl-silanyloxy)-benzyl bromide (14.60 g, 0.034 mol) in acetone and the resulting mixture was heated at reflux for 8 h. Water (20 mL) was then added to the reaction mixture and acetone was evaporated.…”

Section: Synthesis Of 34-bis-(tert-butyl-dimethyl-silanyloxy)-benzylmentioning

confidence: 99%

Synthesis and adhesive property study of polyoxetanes grafted with catechols via Cu(I)-catalyzed click chemistry

Jia

et al. 2014

Polymer

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a b s t r a c tMussel-inspired catechol-containing polymers have drawn great attention due to their outstanding adhesive properties. Catechol-containing polyethylene glycol (cPEG) is a well-studied catechol-containing polymer used for tissue repair. Nevertheless, catechols can only be attached to the chain ends of polyethylene glycols thus the bonding strength of the resulting polymers is limited. Aiming at solving the problem, a series of clickable polyoxetane copolymers with grafted catechol moieties were synthesized in an efficient manner. Upon addition of FeCl 3 as the cross-linker, strong bonding strength of the adhesive was achieved. Polymer containing 15.5 molar percent of catechol showed the strongest bonding strength up to 5.59 MPa on sanded stainless steel. It was found that the triazole groups also contributed to the overall adhesive performance. This polyoxetane-based adhesive also displayed strong bonding ability to a variety of other substrates including porcine skin.

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Section: Synthesis Of 34-bis-(tert-butyl-dimethyl-silanyloxy)-benzylmentioning

confidence: 99%

Synthesis and adhesive property study of polyoxetanes grafted with catechols via Cu(I)-catalyzed click chemistry

Jia

et al. 2014

Polymer

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“…Methylthioether derivatives 3 were converted to methylsulfone compounds 4 by oxidation with hydrogen peroxide in the presence of ammonium molybdate as a catalyst. [13] …”

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confidence: 99%

Rapid, Stable, Chemoselective Labeling of Thiols with Julia–Kocieński‐like Reagents: A Serum‐Stable Alternative to Maleimide‐Based Protein Conjugation

2013

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Cysteine-maleimide chemistry is widely used for peptide and protein modification. However, the formed succinimide linkage is readily hydrolyzed and is susceptible to an exchange reaction in vivo. We demonstrate that methylsulfonyl phenyloxadiazole compounds react specifically with cysteine under various buffer conditions and found that the resulting protein conjugates had superior stability to cysteine-maleimide conjugates in human plasma. This Thiol-Click chemistry promises a new approach to stable protein conjugates and pegylated proteins.

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“…[13] Next, in order to study protein conjugation, fluorescein derivatives of the sulfone and maleimide compounds 7 and 10 were synthesized (Scheme 2). A generalized synthesis is shown in Scheme 1.…”

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confidence: 99%

Rapid, Stable, Chemoselective Labeling of Thiols with Julia–Kocieński‐like Reagents: A Serum‐Stable Alternative to Maleimide‐Based Protein Conjugation

2013

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Eine hervorragende Chemoselektivität für Cystein zeichnet Methylsulfonylphenyloxadiazol‐Verbindungen in verschiedenen Puffern aus. Die resultierenden Proteinkonjugate sind in Humanplasma beständiger als Cystein‐Maleimid‐Konjugate (HSA=Human‐Serumalbumin, MBP‐C‐HA=Maltose bindendes Protein). Diese neue Thiol‐Klickreaktion sollte einen Weg für die Bildung stabiler Proteinkonjugate und PEGylierter Proteine eröffnen.

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Total synthesis of artochamins F, H, I, and J through cascade reactions

Cited by 27 publications

References 101 publications

Synthesis and adhesive property study of polyoxetanes grafted with catechols via Cu(I)-catalyzed click chemistry

Synthesis and adhesive property study of polyoxetanes grafted with catechols via Cu(I)-catalyzed click chemistry

Rapid, Stable, Chemoselective Labeling of Thiols with Julia–Kocieński‐like Reagents: A Serum‐Stable Alternative to Maleimide‐Based Protein Conjugation

Rapid, Stable, Chemoselective Labeling of Thiols with Julia–Kocieński‐like Reagents: A Serum‐Stable Alternative to Maleimide‐Based Protein Conjugation

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