Synthesis and properties of unsymmetrical aryl glucosyl disulfides: models for a new class of cleavable nonionic detergents

Cuomo, John; Merrifield, James H.; Keana, John F. W.

doi:10.1021/jo01309a030

Cited by 26 publications

(16 citation statements)

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“…Deshalb wurde die Trichloracetimidat-Methode auch zur Synthese dieser Verbindung eingesetzt. Dazu wurde die 2,3,4,6-Tetra-0-a~etyl-D-galactose~~) (9) mit Trichloracetonitrit und Natriumhydrid als Base umgesetzt und das Trichloracetimidat 10 in guter Ausbeute als Anomerengemisch ( a : p = I : 2) gewonnen, das aufgrund der P-dirigierenden Wirkung der 2-0-Acetylschutzgruppe direkt eingesetzt wurde. Unter den fiir 3 beschriebenen Bedingungen wurde aus 10 und 2-Propanthiol ausschlieljlich das I-Thio-P-D-galactopyranosid lls24' und daraus durch Natriummethanolatbehandlung das ungeschiitzte Isopropyl-1-thiogalactopyranosid 12az4' in jeweils hoher Ausbeute erhalten.…”

Section: B) 1-thiogalactopyranoside (Schema 2)unclassified

Glycosylimidate, 8. Synthese von 1‐Thioglycosiden

1983

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Das reaktive acetylgeschutzte 0-(a-D-Glucopyranosy1)trichloracetimidat 3 liefert mit S-Nucleophilen unter Bortrifluorid-Ether-Katalyse erwartungsgemll3 unter Inversion der Konfiguration ausschliel3lich 1-Thio-P-D-glucopyranoside. Mit dern entsprechenden benzylgeschiitzten a-Trichloracetirnidat 4 werden unter Retention der Konfiguration ausschliel3lich 1-Thio-a-D-glucopyranoside erhalten. Die Bedeutung von Alkyl-1-thio-B-o-galactopyranosiden zur Enzyminduktion war AnlaR, diese einfache Glycosylubertragung auch zur Synthese von Isopropyl-1-thio-P-Dgalactopyranosid (12a) und des Natriumsalzes von 1-Thio-P-D-galactopyranose (12b) anzuwenden. Glycosylimidates, 8 I). -Synthesis of 1-ThioglycosidesAs expected, the reactive acetyl-protected O-(a-D-glUCOpyranOSy1) trichloroacetimidate 3 reacts with S-nucleophiles and trifluoroborane-ether as catalyst to yield exclusively I-thio-P-D-glucopyranosides with inversion of the configuration. The corresponding benzyl-protected a-trichloroacetimidate 4 affords with retention of the configuration alkyl 1 -thio-a-D-glucopyranosides. The importance of alkyl I-thio-f3-D-galactopyranosides in enzyme induction was reason to apply this convenient and efficient glycosyl-transfer reaction to the synthesis of isopropyl 1-thi0-D-Dgalactopyranoside (12a) and the sodium salt of 1-thio-P-D-galactopyranose (12b), respectively.

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Section: B) 1-thiogalactopyranoside (Schema 2)unclassified

Glycosylimidate, 8. Synthese von 1‐Thioglycosiden

1983

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“…There exists a destructible group between the hydrophobic and hydrophilic portions of cleavable surfactants. The destructible groups are labile under mild conditions such as acid (1-12}, base (13), salt (14), heat (15) and light (16), and they are reactive to neutral molecules (17). Up to now, the main interest has been focused on surfactants with a 1,3-dioxolane ring (1)(2)(3)(4)(5)(6)(7)(8)(9)(10)(11).…”

mentioning

confidence: 99%

Preparation and properties of sulfonate salt‐type cleavable surfactants with a 1,3‐dioxane ring

Wang

Yuan

Liu

et al. 1994

J Americ Oil Chem Soc

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A series of di-anionic cleavable surfactants were prepared by the condensation of aldehydes with 2,2-b/s(hydroxymethyll-l,3-propanediol, followed by reaction with 1,3propanesultone in the presence of sodium hydride. Surfactant 5a had a different 1H nuclear magnetic resonance spectrum in D20 than products 5b-d. This was rationalized by its different conformation, which originates from the self-coiling of its alkyl chain. The critical micelle concentrations, Krafft points and hydrolysis properties of these surfactants were determined.

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“…For example, reaction of a thiosugar with arylsulfenylchloride produced a series of unsymmetrical aryl glycosyl disulfides as potential solubilizing agents to isolate and purify membrane proteins. 53 Dithiocarbamates have been another functionality used to introduce sulfur at the anomeric position. Treatment of a glycosyl dithiocarbamate with a strong base (e.g.…”

Section: Synthesis Via Nucleophilic Sulfur-based Carbohydratesmentioning

confidence: 99%

“…107 As long ago as the 1980s, the use of unsymmetrical glycosyl disulfides as detergents was proposed to solve this problem. 53 The idea behind this approach explored the amphiphilic character of glycosyl disulfides, and the cleavability of the disulfide linkage by mild protein-compatible agents, and that the thioglucose and apolar aglycone produced in the cleavage reaction should be readily removed by dialysis. Therefore the authors claimed that unprotected unsymmetrical disulfides could be considered as biologically compatible detergents and an alternative to ionic detergents for the isolation of MPs.…”

Section: Glycosyl Disulfides As Chemically-cleavable Detergentsmentioning

confidence: 99%