title: Expeditious synthesis of enantiopure, orthogonally protected bis-α-amino acids (OPBAAs) and their use in a study of Nod1 stimulation.
abstract: A convenient approach towards the synthesis of orthogonally protected chiral bis-α-amino acids (OPBAAs) is described. The key transformations include: (1) a highly stereoselective conjugation (alkylation) of the Schöllkopf bis-lactim ethers and oxazolidinyl alkyl halides to build a backbone skeleton; and (2) our orthogonal protection strategy. A series of enantiopure OPBAAs bearing a variety of alkyl chain as a spacer; two stereogenic centers; and three protecting groups were prepared as examples. These versatile molecules were applied to the synthesis of biologically interesting di- or tri-peptide analogues, including chiral iE-meso-DAP and A-iE-meso-DAP, for the study of Nod1 activation in the innate immune response.
authors.affiliation: The Genomics Research Center, Academia Sinica, No. 128, Academia Road Sec. 2, Nankang District, Taipei, 11529 (Taiwan), Fax: (+886) 2-27899931.
authors.forename: Po-Ting
authors.initials: PT
authors.lastname: Chen
authors.forename: Cheng-Kun
authors.initials: CK
authors.lastname: Lin
authors.forename: Chih-Ju
authors.initials: CJ
authors.lastname: Tsai
authors.forename: Duen-Yi
authors.initials: DY
authors.lastname: Huang
authors.forename: Fu-Yao
authors.initials: FY
authors.lastname: Nien
authors.forename: Wan-Wan
authors.initials: WW
authors.lastname: Lin
authors.forename: Wei-Chieh
authors.initials: WC
authors.lastname: Cheng
mesh_terms: D000478:Alkylation; D000596:Amino Acids / Q000737:chemistry; D057809:HEK293 Cells; D006801:Humans; D007113:Immunity, Innate / Q000187:drug effects; D016328:NF-kappa B / Q000235:genetics / Q000378:metabolism; D053474:Nod1 Signaling Adaptor Protein / Q000235:genetics / Q000378:metabolism*; D010455:Peptides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D013237:Stereoisomerism
chemical_list: D000596:Amino Acids; D016328:NF-kappa B; C119067:NOD1 protein, human; D053474:Nod1 Signaling Adaptor Protein; D010455:Peptides
keywords: Nod1; Schöllkopf bis-lactim ethers; amino acids; immunology; innate immunity; synthetic methods