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Expeditious Synthesis of Enantiopure,Orthogonally Protected Bis‐α‐Amino Acids (OPBAAs) and their Use in a Study of Nod1 Stimulation |
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| Authors: | Po‐Ting Chen Cheng‐Kun Lin Chih‐Ju Tsai Dr. Duen‐Yi Huang Fu‐Yao Nien Dr. Wan‐Wan Lin Prof. Dr. Wei‐Chieh Cheng |
| Affiliation: | 1. The Genomics Research Center, Academia Sinica, No. 128, Academia Road Sec. 2, Nankang District, Taipei, 11529 (Taiwan), Fax: (+886)?2‐27899931;2. Department of Pharmacology, College of Medicine, National Taiwan University, No. 1, Jen‐Ai Road, Section 1, Taipei, 10051 (Taiwan);3. Department of Chemistry, National Cheng Kung University, No. 1, University Road, Tainan City, 701 (Taiwan);4. Graduate Institute of Medical Sciences, Taipei Medical University, No. 250, Wuxing Street, Taipei, 11031 (Taiwan) |
| 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. |
| Keywords: | amino acids immunology innate immunity Nod1 Schö llkopf bis‐lactim ethers synthetic methods |