Reduction of Disulfides with Tributylphosphine.

Humphrey, Ray E.; Potter, Joseph L.

doi:10.1021/ac60220a049

Cited by 85 publications

(47 citation statements)

References 12 publications

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“…Disulfide moieties can be reduced to the thiol groups by making use of a reducing agent [23]. To demonstrate this in our present work, the obtained hyperbranched polymer was treated by n-tributylphosphine, resulting in the formation of linear poly(NIPAM).…”

Section: Degradation Of the Hyperbranched Polymermentioning

confidence: 87%

Thermoresponsive hyperbranched glycopolymers: Synthesis, characterization and lectin interaction studies

Vandewalle

Wallyn

Chattopadhyay

et al. 2015

European Polymer Journal

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a b s t r a c tPreparation of stimuli-responsive hyperbranched glycopolymers that are able to simultaneously enhance and control the lectin-polymer interaction has been challenging. Hyperbranched glycopolymers have been prepared in which thermo-responsive Poly(N-isopropylacrylamide) [poly(NIPAM)], connected by redox-responsive disulfide bonds, forms the skeleton and for which mannose units are present at each branching point. Degradation of the hyperbranched structure via chemical reduction of the disulfide bond was demonstrated. Moreover, the thermoresponsive behaviour of the glycopolymer was studied. Finally, the lectin-polymer interaction was investigated in order to understand the influence of both the polymer concentration and different chain conformations below and above the cloud point, respectively.

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Section: Degradation Of the Hyperbranched Polymermentioning

confidence: 87%

Thermoresponsive hyperbranched glycopolymers: Synthesis, characterization and lectin interaction studies

Vandewalle

Wallyn

Chattopadhyay

et al. 2015

European Polymer Journal

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“…Prior to thiol analysis, slurries were allowed to settle and a 2 ml aliquot of the supernatant was filtered (0.2 pm, Nucleopore) and derivatized. Some sediment slurries were treated with a specific S-S cleaving reagent, tributylphosphine (13), in order to evaluate the degree to which thiols were bound via disulfide linkages. The reagent was added to a final concentration of 0.5-1.0 ml per liter slurry.…”

Section: Methodsmentioning

confidence: 99%

Biogeochemical Cycling of Sulfur

Mopper

Taylor

1986

ACS Symposium Series

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Thiols are major intermediates in the microbial cycling of sulfur and, because of their high reactivity, they may also play important roles in geochemical processes. Preliminary studies using a new, highly sensitive HPLC assay revealed that thiols are present at concentrations up to 100μΜ in intertidal marine sediments from Biscayne Bay (FL). Methanethiol (MeS) and 3-mercaptopropionate (MP) were the major thiols found. The presence of the latter compound suggests that, in addition to protein degradation, anaerobic decomposition of dimethylpropiothetin (DMPT), a major sulfur compound of marine algae and higher plants, may be an important source of thiols and a significant degradation pathway for DMPT in the environment. Acrylic acid produced from this pathway readily adds HS across the double bond, via Michael addition, to form 3-mercaptopro pionate. Alternatively, this thiol may be formed directly from DMPT by successive anaerobic demethylations; however the biochemical feasibility of this pathway is presently not known. Addition of a specific disulfide cleaving reagent to sediments revealed that thiols are dominantly present in bound forms. Binding of thiols to sediment particles may be an important mechani sm for the incorporation of organic sulfur into geopolymers. Diagenesis of organic matter i n the water column and sediments resultsi n the production of a wide variety of organosulfur compounds.Most studies involving these compounds i n the marine environment have focussed on gaseous and hydrophobic species (1 ). In contrast, information regarding reduced, hydrophilic sulfur organics, in particular the thiols (general formula R-SH, where R is an organic group), is almost nonexistent.

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“…Surprisingly, the speed of disulfide formation was dependent on the solvent. The disulfides were reduced to the corresponding thiols with either PBu 3 in THF/H 2 O [55] or dithiothreitol [56] in MeOH in quantitative yields.…”

mentioning

confidence: 99%

A Direct Synthesis of Nucleoside Analogs Homologated at the 3′‐ and 5′‐Positions

Schmidt

Eschgfäller

Benner

2003

Helvetica Chimica Acta

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A new route is presented to prepare analogs of nucleosides homologated at the 3'-and 5'-positions. This route, applicable to both the d-and l-enantiomeric forms, is suitable for the preparation of monomeric bishomonucleosides needed for the synthesis of oligonucleotide analogs. It begins with the known monobenzyl ether 3 of pent-2-yne-1,5-diol, which is reduced to alkenol 4. Sharpless asymmetric epoxidation of 4, followed by opening of the epoxide 5 with allylmagnesium bromide, gives a mixture of diols 6 and 7. Protection of the primary alcohol as a silyl ether followed by treatment with OsO 4 , NaIO 4 , and mild acid in MeOH, followed by reduction, yields (2R,3R) {{[(tert-butyl)diphenylsilyl]oxy}methyl}tetrahydro-2-(2-hydroxyethyl)-5-methoxyfuran ( methyl 3-{{[(tert-butyl)diphenylsilyl]oxy}methyl}-2,3,5-trideoxy-a/b-d-erythro-hexafuranoside; 10) (Scheme 1). Protected nucleobases are added to this skeleton with the aid of trimethylsilyl triflate (Scheme 2). The o-toluoyl (2-MeC 6 H 4 CO) and p-anisoyl (4-MeOC 6 H 4 CO) groups were used to protect the exocyclic amino group of cytosine. The bis-homonucleoside analogs 11 and 14a are then converted to monothiol derivatives suitable for coupling (Schemes 3 and 4) to oligonucleotide analogs with bridging S-atoms. This synthesis replaces a much longer synthesis for analogous nucleoside analogs that begins with diacetoneglucose ( 1,2 : 5,6-di-Oisopropylideneglucose), with the stereogenic centers in the final products derived from the Sharpless asymmetric epoxidation. The new route is useful for large-scale synthesis of these building blocks for the synthesis of oligonucleotide analogs.

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Reduction of Disulfides with Tributylphosphine.

Cited by 85 publications

References 12 publications

Thermoresponsive hyperbranched glycopolymers: Synthesis, characterization and lectin interaction studies

Thermoresponsive hyperbranched glycopolymers: Synthesis, characterization and lectin interaction studies

Biogeochemical Cycling of Sulfur

A Direct Synthesis of Nucleoside Analogs Homologated at the 3′‐ and 5′‐Positions

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