title: A concise approach to the synthesis of the unique N-mannosyl d-β-hydroxyenduracididine moiety in the mannopeptimycin series of natural products.
abstract: The asymmetric synthesis of the orthogonally protected N-mannosyl d-β-hydroxyenduracididine (N-Man-d-βhEnd) is described, starting from enantiopure silylated (S)-serinol. The key steps are: (i) glycosylamine formation between protected serinol and a benzylated d-mannose; (ii) guanidinylation; and (iii) cyclic guanidine formation. This synthesis constitutes a breakthrough in our studies towards a total synthesis of mannopeptimycin and should also allow for other studies in the field of mannopeptimycin research, including the synthesis of derivatives.
authors.affiliation: Genomics Research Center, Academia Sinica, 128, Section 2, Academia Road, Taipei, 11529, Taiwan. wcheng@gate.sinica.edu.tw.
authors.forename: Cheng-Kun
authors.initials: CK
authors.lastname: Lin
authors.affiliation: Genomics Research Center, Academia Sinica, 128, Section 2, Academia Road, Taipei, 11529, Taiwan. wcheng@gate.sinica.edu.tw.
authors.forename: Wen-Yi
authors.initials: WY
authors.lastname: Yun
authors.affiliation: Department of Chemistry, National Cheng Kung University, 1, University Road, Tainan City, 701, Taiwan.
authors.forename: Lin-Ting
authors.initials: LT
authors.lastname: Lin
authors.affiliation: Genomics Research Center, Academia Sinica, 128, Section 2, Academia Road, Taipei, 11529, Taiwan. wcheng@gate.sinica.edu.tw.
authors.forename: Wei-Chieh
authors.initials: WC
authors.lastname: Cheng
mesh_terms: D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry; D006020:Glycopeptides / Q000138:chemical synthesis* / Q000737:chemistry; D008362:Mannosides / Q000138:chemical synthesis* / Q000737:chemistry; D008968:Molecular Conformation; D011759:Pyrrolidines / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D001688:Biological Products; D006020:Glycopeptides; D008362:Mannosides; D011759:Pyrrolidines; C478082:mannopeptimycin