{"doi":"10.1002/ejoc.200300303","title":"Synthesis of Oligoarabinofuranosides from the Mycobacterial Cell Wall","abstract":"<jats:title>Abstract</jats:title><jats:p>Oligoarabinofuranosides <jats:bold>1</jats:bold>−<jats:bold>4</jats:bold>, fragments of the arabinan components found in the mycobacterial cell wall have been synthesized. <jats:bold>1</jats:bold> and <jats:bold>2 </jats:bold>are representative of the structural features of the internal core of arabinogalactan, arabinomannan and lipoarabinomannans. <jats:bold>3</jats:bold> is the capping motif of the lipoarabinomannan of <jats:italic>Mycobacterium tuberculosis</jats:italic> and <jats:italic>M. bovis</jats:italic> BCG while <jats:bold>4 </jats:bold>is the hexasaccharide found at the non‐reducing end of arabinogalactan. Complete stereocontrol was achieved for the elaboration of glycosidic linkages between arabinofuranoside units: α‐glycosides were obtained by participation of an ester or carbonate group on the 2‐position, while β‐arabinofuranosides were secured by an internal aglycon delivery approach. (© Wiley‐VCH Verlag GmbH &amp; Co. KGaA, 69451 Weinheim, Germany, 2003)</jats:p>","journal":"European Journal of Organic Chemistry","year":2003,"id":671007,"datarank":3.0659870111634673,"base_score":4.007333185232471,"endowment":4.007333185232471,"self_citation_contribution":0.6010999777848708,"citation_network_contribution":2.4648870333785964,"self_endowment_contribution":0.6010999777848708,"citer_contribution":2.4648870333785964,"corpus_percentile":null,"corpus_rank":null,"citation_count":54,"citer_count":53,"citers_with_citation_signal":51,"citers_with_endowment":51,"datacite_reuse_total":0,"is_dataset":false,"is_dataset_confidence":null,"is_data_producer":false,"deposit_databanks":null,"is_oa":false,"file_count":0,"downloads":0,"has_version_chain":false,"published_date":null,"fair_score":null,"fair_percentile":null,"algorithm_id":"datarank_citation_only_1hop_v6","ranking_scope":"data_only","authors":[{"id":1752891,"name":"Sylvie Sanchez","orcid":null,"position":1,"is_corresponding":false},{"id":1752893,"name":"Toufiq Bamhaoud","orcid":null,"position":2,"is_corresponding":false},{"id":1286494,"name":"Jacques Prandi","orcid":null,"position":3,"is_corresponding":false},{"id":1752889,"name":"Karine Marotte","orcid":null,"position":0,"is_corresponding":false}],"reference_count":0,"raw_metadata":{"has_enrichment":true,"resolved":true,"title":"Synthesis of Oligoarabinofuranosides from the Mycobacterial Cell Wall","abstract":"<jats:title>Abstract</jats:title><jats:p>Oligoarabinofuranosides <jats:bold>1</jats:bold>−<jats:bold>4</jats:bold>, fragments of the arabinan components found in the mycobacterial cell wall have been synthesized. <jats:bold>1</jats:bold> and <jats:bold>2 </jats:bold>are representative of the structural features of the internal core of arabinogalactan, arabinomannan and lipoarabinomannans. <jats:bold>3</jats:bold> is the capping motif of the lipoarabinomannan of <jats:italic>Mycobacterium tuberculosis</jats:italic> and <jats:italic>M. bovis</jats:italic> BCG while <jats:bold>4 </jats:bold>is the hexasaccharide found at the non‐reducing end of arabinogalactan. Complete stereocontrol was achieved for the elaboration of glycosidic linkages between arabinofuranoside units: α‐glycosides were obtained by participation of an ester or carbonate group on the 2‐position, while β‐arabinofuranosides were secured by an internal aglycon delivery approach. (© Wiley‐VCH Verlag GmbH &amp; Co. 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