Glycosylation with N-Troc-protected glycosyl donors

Ellervik, Ulf; Magnusson, Göran

doi:10.1016/0008-6215(95)00318-5

Cited by 118 publications

(62 citation statements)

References 22 publications

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“…However, commonly used N-protecting groups like N-dichlorophthaloyl, [71] Ntetrachlorophthaloyl, [72][73][74] N-chloroacetyl, [75] N-trichloroacetyl, [76,77] N-trichloroethoxycarbonyl, [78,79] or N,N-diacetyl [80] were not applicable here due to their high sensibility under conditions required for saponification of the tether. The use of 2-azido-2-deoxy glucose derivatives as starting materials appeared impractical as well, because this avenue would require employment of triflyl azide which is, however, inconvenient on a large scale.…”

Section: Resultsmentioning

confidence: 99%

Synthesis of Pentasaccharide Fragments Related to the O‐Specific Polysaccharide of Shigella flexneri Serotype 1a

Lemanski

Ziegler

2006

Eur J Org Chem

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The synthesis of the pentasaccharide 5‐aminopentylglycosides α‐L‐Rhap‐(1→3)‐[α‐D‐Glcp‐(1→4)]‐β‐D‐GlcpNAc‐(1→2)‐α‐L‐Rhap‐(1→2)‐α‐L‐Rhap‐1‐O‐(CH2)5NH2 (29) andα‐L‐Rhap‐(1→3)‐α‐L‐Rhap‐(1→3)‐[α‐D‐Glcp‐(1→4)]‐β‐D‐GlcpNAc‐(1→2)‐α‐L‐Rhap‐1‐O‐(CH2)5NH2 (28), related to the O‐specific polysaccharide of Shigella flexneri serotype 1a by coupling of the suitably protected trisaccharides α‐D‐Glcp‐(1→4)‐β‐D‐Glcp(1→2)‐α‐L‐Rhap‐1‐O‐(CH2)5NH2 (23) and α‐L‐Rhap‐(1→3)‐[α‐D‐Glcp‐(1→4)]‐β‐D‐Glcp‐1‐SPh (26) with the corresponding rhamnosyl glycosides α‐L‐Rhap‐(1→3)‐α‐L‐Rhap‐1‐SEt (17) and α‐L‐Rhap‐(1→3)‐α‐L‐Rhap‐1‐O‐(CH2)5NH2 (13), is described. Building blocks 23 and 26 were prepared by intramolecular glycosylation of an unsymmetrically tethered cellobiosamine derivative. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)

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Section: Resultsmentioning

confidence: 99%

Synthesis of Pentasaccharide Fragments Related to the O‐Specific Polysaccharide of Shigella flexneri Serotype 1a

Lemanski

Ziegler

2006

Eur J Org Chem

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“…However, the yield could be significantly improved by using guanidine/guanidinium nitrate reagent (G/GHNO 3 ) 18) that provided 12 in 89% yield. Benzylidenation 19) of disaccharide 12 produced acceptor 13, which was subjected to glycosylation with donor 14 20) 21) by deacetylation, benzylidenation, chloroacetylation, and reductive ring-opening of the benzylidene acetal as previously described.…”

Section: Resultsmentioning

confidence: 99%

“…Column chromatography was carried out on Silica Gel 60 (E. Merck). 21) were prepared as reported. Benzoylceramide 10 was prepared from phytosphingosine, which was purchased from Degussa (The Netherlands) by the conventional four-step procedure.…”

Section: Methodsmentioning

confidence: 99%

Synthetic Studies on Glycosphingolipids from Protostomia Phyla: Synthesis of Glycosphingolipids from the Parasite Schistosoma mansoni

Kanaya

Yagi

Schweizer

et al. 2010

CHEMICAL & PHARMACEUTICAL BULLETIN

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“…[20] However, the synthesis that used the thioglycosyl donor 11 (for the synthesis of 11 see Supporting Information) [21] proved to be the most convenient method. Compound 11 could be obtained in 41 % yield starting from D-glucosamine by following known procedures.…”

Section: Synthesis Of Nls Peptides With Different Modificationsmentioning

confidence: 99%

Influence of Serine O‐Glycosylation or O‐Phoshorylation Close to the vJun Nuclear Localisation Sequence on Nuclear Import

et al. 2006

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Nuclear import triggered by the nuclear-localisation sequence (NLS) of the viral Jun (vJun) protein is mediated by phosphorylation of a serine close to the NLS. Since phosphorylation and glycosylation of serine residues are often in a reciprocal "yin-yang" relationship, we investigated whether glycosylation of this serine with O-linked N-acetylglucosamine (O-GlcNAc) would also regulate nuclear import via the vJun NLS. Peptides containing the vJun NLS with an adjacent O-phosphorylated, O-GlcNAc-functionalised or unmodified serine, and equipped with an N-terminal biotin or a 7-nitrobenz-2-oxa-1,3-diazolyl (NBD) fluorescent label, were synthesised on the solid phase by means of an Fmoc/Boc strategy and a Pd0-sensitive HYCRON linker. Fluorescence-polarisation measurements on the NBD-labelled peptides indicated that modification with phosphate or O-GlcNAc leads to a decrease in affinity to the import-mediating adapter protein, importin alpha, of about one order of magnitude compared to the unmodified NLS. Microinjection of biotinylated NLS peptide conjugated with fluorescently labelled avidin into NIH/3T3 and MDCK cells, revealed that avidin-unmodified-NLS peptide was rapidly imported into the nucleus. However, either phosphate or O-GlcNAc next to the NLS caused almost complete exclusion of the protein conjugate from nuclear import. These findings indicate that nuclear import by the vJun NLS might not be regulated by a "yin-yang" modification of an adjacent serine with phosphate or O-GlcNAc. Rather, negative regulation of binding between the polybasic NLS and importin by a negatively charged or a bulky, uncharged residue appears likely.

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Glycosylation with N-Troc-protected glycosyl donors

Cited by 118 publications

References 22 publications

Synthesis of Pentasaccharide Fragments Related to the O‐Specific Polysaccharide of Shigella flexneri Serotype 1a

Synthesis of Pentasaccharide Fragments Related to the O‐Specific Polysaccharide of Shigella flexneri Serotype 1a

Synthetic Studies on Glycosphingolipids from Protostomia Phyla: Synthesis of Glycosphingolipids from the Parasite Schistosoma mansoni

Influence of Serine O‐Glycosylation or O‐Phoshorylation Close to the vJun Nuclear Localisation Sequence on Nuclear Import

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