Recent applications of thiol–ene coupling as a click process for glycoconjugation

Dondoni, Alessandro; Marra, Alberto

doi:10.1039/c1cs15157f

Cited by 270 publications

(175 citation statements)

References 65 publications

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“…After successful discovery of click chemistry concept by Sharpless and Meldal, it is easy to perform polymer modification with high yield under mild conditions, such as rapid, stereospecific, orthogonal and no by-product coherent with the green chemistry [26]. Today, a series of reactions including Huisgen type Cu(I) catalyzed cycloaddition (CuAAC) [27,28], thiol-ene [29][30][31] and Diels-Alder [32] are recognized as well-known click chemistry reactions [33]. Modification of polymers with CuAAC click reaction is very general, robust and particularly simple compared to other click chemistry reactions [34][35][36][37].…”

Section: Introductionmentioning

confidence: 99%

Polypropylene-based graft copolymers via CuAAC click chemistry

Açık¹,

Sey²,

Taşdelen³

2018

Express Polym. Lett.

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Abstract. Graft copolymers from commercial chlorinated polypropylene (PP-Cl) possessing either poly(ethylene glycol) (PEG) or poly(ɛ-caprolactone) (PCL) grafts are synthesized by copper (I)-catalyzed azide-alkyne cycloaddition 'click' reaction (CuAAC). For this purpose, azido-functional polypropylene is prepared by nucleophilic substitution of chlorine groups of PP-Cl with azidotrimethylsilane-tetrabutylammonium fluoride. Whereas, the clickable alkyne end-functional PEG and PCL are independently synthesized by esterification reaction of poly(ethylene glycol) methyl ether with 4-pentyonic acid at room temperature and ring-opening polymerization of ε-caprolactone using stannous octoate as catalyst and propargyl alcohol as initiator. Finally, the corresponding graft copolymers, PP-g-PEG and PP-g-PCL, with different surface properties were successfully synthesized by CuAAC 'click' reaction under mild condition. Spectral, chromatographic and thermal analyses at various stages prove the formation of desired polypropylene-based graft copolymers with well-defined properties. Furthermore, the water contact angle values of PP-Cl, PP-g-PEG and PP-g-PCL are found as 90±1°, 78±1.8° and 83±2.1°, respectively.

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Section: Introductionmentioning

confidence: 99%

Polypropylene-based graft copolymers via CuAAC click chemistry

Açık¹,

Sey²,

Taşdelen³

2018

Express Polym. Lett.

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“…26 Much less work has been devoted to additions of thiols to sugar 'ene'-s in which the double bond is part of or directly attached to the sugar ring: thus, additions to sugar derived enones 27 and some reactions of endo28e30 and recently also exo-glycals 30e33 as well as derivatives with an exomethylene group in the 4-and a 5-position of a furanoside and a pyranoside, 34 respectively, and a 3-exomethylene-glucofuranose 31,32 have been reported.…”

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confidence: 99%

Photoinitiated hydrothiolation of pyranoid exo-glycals: the d-galacto and d-xylo cases

József

Juhász

Illyés

et al. 2015

Carbohydrate Research

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Exclusive regio-and stereoselectivity with exo-galactal. Exclusive regio-and very high stereoselectivity with exo-xylal. Disaccharide mimicks of Gly-CH 2 -S-Gly scaffolds. Contents lists available at ScienceDirectCarbohydrate Research j o u r n a l h o m e p a g e : w w w . e l s e v i e r . c o m/ l o c a t e / c a r r e s a b s t r a c tRadical-mediated addition reactions of thiols to O-peracetylated exo-galactal and exo-xylal with 2,2-dimethoxy-2-phenylacetophenone as the photoinitiator resulted in high yielding formation of the corresponding b-D-glycopyranosylmethyl-sulfide derivatives (2,6-anhydro-1-deoxy-1-S-substituted-1-thioalditols) with exclusive regio-and very high stereoselectivity, including disaccharide mimicks with Gly-CH 2 -S-Gly scaffolds. © 2015 Published by Elsevier Ltd.Glycomimetic compounds are widely used for deciphering the biological roles of carbohydrate derivatives.1 Glycomimetics resemble natural carbohydrates in their structure and/or biological function and often serve as lead compounds for drug design. 2 One of the most important features of such compounds is the hydrolytic stability of the bond(s), which replace the natural O-glycosidic linkage(s). A wide range of such replacements were suggested, among others S-glycosides and C-glycosyl derivatives with a sulfur atom or a methylene group, respectively, in the position of the glycosidic oxygen. 1 In addition, in a number of examples two (or even more) atoms are inserted between the glycon and aglycon 3 in the form of e.g., SeS, 4e8 SeSe, 8e10 SO 2 eN, 11e13 NeC(¼O)eN linking moieties. 14e17Carbohydrate derivatives displaying Gly-CH 2 -S-R scaffolds are much less represented among glycomimetics although some synthetic methods, mostly limited to the application of O-perbenzylated exo-glycals, can be found in the literature. Thus, exo-glucal was transformed in several steps into a Glc-CH 2 -I derivative, 18e20 which was reacted under basic conditions with aliphatic and aromatic thiols including sugar derivatives to give the above structures. Ring openings by nucleophiles of an exo-glucal-derived spiro-epoxide 21 as well as a spiro-episulfonium ion 22 resulted in ulose derivatives featuring the above structure. Radical-mediated addition of AcSH to exo-glycals furnished S-(b-D-glycosylmethyl) thioacetates. 23The thiol-ene addition chemistry, 24,25 either in ionic or radicalmediated versions, has found several applications in carbohydrate chemistry for S-glycoconjugation, wherein the sugar derivative generally plays the role of the thiol or is functionalized by O-or Cappended unsaturated moieties. 26 Much less work has been devoted to additions of thiols to sugar 'ene'-s in which the double bond is part of or directly attached to the sugar ring: thus, additions to sugar derived enones 27 and some reactions of endo28e30 and recently also exo-glycals 30e33 as well as derivatives with an exomethylene group in the 4-and a 5-position of a furanoside and a pyranoside, 34 respectively, and a 3-exomethylene-glucofuranose 31,32 have been report...

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“…Radical addition of the Boc-protected aminoethanethiol 3 to the allyl glycoside 20 was carried out smoothly using a-azobisisobutyronitrile (AIBN) as a radical initiator to furnish linker-attached trisaccharide 22. 33 Deprotection of TBS (/ 23), followed by in situ acetylation provided the compound 24, which was subjected to TFA in DCM afforded glycosyl amine 25 in good yield. Condensation of amine 25 with 1,3,5-benzenetricarbonyl trichloride 4 gave C 3 -symmetric product 26 in the presence of TEA 34 in 67% yield, which was further deacylated to achieve the cluster compound 2 in a quantitative yield.…”

Section: Resultsmentioning

confidence: 99%