Synthesis of deoxy and acylamino derivatives of lactose and use of these for probing the active site of Neisseria meningitidis N-acetylglucosaminyltransferase

Westerlind, Ulrika; Hagback, Per; Tidbäck, Björn; Wiik, Lotta; Blixt, Ola; Razi, Nahid; Norberg, Thomas

doi:10.1016/j.carres.2004.11.017

Cited by 19 publications

(9 citation statements)

References 11 publications

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“…The synthesis of deoxy sugars, especially the synthesis of 2-deoxyglycosides and their derivatives, has drawn increasing attention from carbohydrate chemists because many bioactive natural products have deoxyglycosides as the main constituents of glycosidic chains that play significant roles in bioactivity. − Usually, these deoxy carbohydrate derivatives were synthesized through the reduction of glycals, glyco-epoxides, glycosides with halides, − and glycosides with a thiocarbonyl group − and thioacetate group. , Recently, we have developed a method to obtain the deoxyglycosides through desulfurization of glycoside thiols under ultraviolet light (Scheme a) in order to overcome the shortcomings of Raney nickel catalyzed reduction of a thioacetate group. , In this method, the acylated substrates have to be deprotected in the first step to form glycosyl thiols, which is then desulfurized in the second step to form unprotected deoxy glycosides. This method may be limited in many applications in which acylated deoxyglycoside derivatives are key intermediates (Scheme b). − ,, Therefore, we wondered if we could develop a method for removal of a thioacetyl group via desulfurization under UV light to obtain acylated deoxyglycoside derivatives.…”

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A One-Pot Method for Removal of Thioacetyl Group via Desulfurization under Ultraviolet Light To Synthesize Deoxyglycosides

Zhou

Luo

et al. 2019

Org. Lett.

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We herein developed an efficient method for removing thioacetyl to synthesize acylated deoxy glycosides in a one-pot reaction, where the thioacetyl was selectively deacetylated by hydrazine hydrate in DMF within 2–5 min at room temperature, followed by desulfurization under UV light for 1–2 h in the presence of TCEP·HCl. The method was then used to synthesize 2-deoxy glycosides with absolute α/β-configuration via stereoselective control of C-2 thioacetate in glycosylation.

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confidence: 99%

A One-Pot Method for Removal of Thioacetyl Group via Desulfurization under Ultraviolet Light To Synthesize Deoxyglycosides

Zhou

Luo

et al. 2019

Org. Lett.

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“…Similarly β‐ D ‐lactose octa‐acetate28 was treated directly with the linker to provide (3′‐bromopropoxy)‐β‐ D ‐lactose hepta‐acetate. Subsequent treatment with ciprofloxacin methyl ester and base‐mediated deprotection furnished lacCpf 3 .…”

Section: Resultsmentioning

confidence: 99%

Probing Bacterial Uptake of Glycosylated Ciprofloxacin Conjugates

et al. 2014

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Mono- and disaccharide-functionalised conjugates of the fluoroquinolone antibiotic ciprofloxacin have been synthesised and used as chemical probes of the bacterial uptake of glycosylated ciprofloxacin. Their antimicrobial activities against a panel of clinically relevant bacteria were determined: the ability of these conjugates to inhibit their target DNA gyrase and to be transported into the bacteria was assessed by using in vivo and in vitro assays. The data suggest a lack of active uptake through sugar transporters and that although the addition of monosaccharides is compatible with the inhibition of DNA gyrase, the addition of a disaccharide results in a significant decrease in antimicrobial activity.

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“…159 For example, lactose benzylidene derivative 64 was treated with NBS to be transformed into bromide 65 , which under hydrogenolysis afforded the 6′-deoxy derivative 66 (Scheme 28). 160…”

Section: Deoxygenation Methodsmentioning

confidence: 99%