2014
DOI: 10.3762/bjoc.10.144
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Synthesis of the first examples of iminosugar clusters based on cyclopeptoid cores

Abstract: SummaryCyclic N-propargyl α-peptoids of various sizes were prepared by way of macrocyclizations of linear N-substituted oligoglycines. These compounds were used as molecular platforms to synthesize a series of iminosugar clusters with different valency and alkyl spacer lengths by means of Cu(I)-catalysed azide–alkyne cycloadditions. Evaluation of these compounds as α-mannosidase inhibitors led to significant multivalent effects and further demonstrated the decisive influence of scaffold rigidity on binding aff… Show more

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Cited by 38 publications
(35 citation statements)
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“…The syntheses of the cyclic hexamer, cyclo-(Npa) 6 1, and of the cyclic octamer, cyclo-(Npa) 8 2, have been previously reported. 13 In order to obtain crystals suitable for X-ray diffraction analysis we attempted several crystallization trials.…”
Section: Resultsmentioning
confidence: 99%
“…The syntheses of the cyclic hexamer, cyclo-(Npa) 6 1, and of the cyclic octamer, cyclo-(Npa) 8 2, have been previously reported. 13 In order to obtain crystals suitable for X-ray diffraction analysis we attempted several crystallization trials.…”
Section: Resultsmentioning
confidence: 99%
“…These scaffolds were efficiently prepared [ by way of iterative submonomer solid-phase synthesis followed by cyclization in high dilution conditions, leading to ones of the largest cyclopeptoids prepared by head-to-tail coupling strategy (Scheme S3 in the Supporting Information). [13,17] The decisive microwave-assisted CuAACr eactionw as found to proceedsmoothly to provide the desired 18-to 48-valent pera-cetylatedDNJ clusters 6 in 32 to 77 %yields which were deprotected by using basic anion exchange resin. These compounds were evaluated as inhibitors of Jack bean a-mannosidase (JBaman), the glycosidase which has shown the largest responses to multivalent inhibitor presentationtodate.…”
mentioning
confidence: 98%
“…2a [6] 1188 [6] --2b 31 0.5 AE 1.5 18 6 1b [10] 21 0.019 AE 0.003 [10] 9895 471 3c [13] 10 5 AE 1 [13] the case of the mannosidase alone, the image showed clear clusters of approximately 10 20nm ( Figure 2, left, light-colored frame)m atching the size of one homodimer (LH) 2 .…”
mentioning
confidence: 99%
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