Expeditious Synthesis of Enantiopure, Orthogonally Protected Bis‐α‐Amino Acids (OPBAAs) and their Use in a Study of Nod1 Stimulation. Issue 2 (12th December 2014)

• Record Type: Journal Article
• Authors: Chen, Po‐Ting; Lin, Cheng‐Kun; Tsai, Chih‐Ju; Huang, Duen‐Yi; Nien, Fu‐Yao; Lin, Wan‐Wan; Cheng, Wei‐Chieh
• Is Part Of: Chemistry, an Asian journal. Volume 10:Issue 2(2015:Feb.)
• Page Start: 474
• Page End: 482
• Publication Date: 2014-12-12
• Subjects: Chemistry -- Periodicals; 540.5
• DOI: 10.1002/asia.201403173
• Languages: English
• ISSNs: 1861-4728

Abstract

<abstract abstract-type="main" xml:lang="en"> <title>Abstract</title> <p>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‐<italic>meso</italic>‐DAP and A‐iE‐<italic>meso</italic>‐DAP, for the study of Nod1 activation in the innate immune response.</p> </abstract>