biostudies-literatureKrow GRNCRR NIH HHSNIAMS NIH HHS5438-41https://www.ebi.ac.uk/biostudies/studies/S-EPMC2993784biostudies-literatureUnknown12(23)CD spectra for homooligomers (n = 4, 6, 8) of (1S,4R,5R)-5-syn-carboxy-2-azabicyclo[2.1.1]hexane (MPCA), a methano-bridged pyrrolidine β-carboxylic acid, suggest an ordered secondary structure. Even in the absence of internal hydrogen bonding, solution NMR, X-ray, and in silico analyses of the tetramer are indicative of conformations with trans-amides and C(5)-amide-carbonyls oriented toward the C(4) bridgehead. This highly constrained β-amino acid could prove useful in the ongoing development of well-defined foldamers.Organic lettersOligomers of a 5-carboxy-methanopyrrolidine β-amino acid. A search for order.PMC2993784S10 RR013790-01R01 AR044276R01 AR044276-15AR044276S10 RR13790S10 RR013790DeBrosse CKrow GRSonnet PERaines RTCentafont RRoss CWLiu NShoulders MDLin GCarroll PJSender MfalseOligomers of a 5-carboxy-methanopyrrolidine β-amino acid. A search for order.CD spectra for homooligomers (n = 4, 6, 8) of (1S,4R,5R)-5-syn-carboxy-2-azabicyclo[2.1.1]hexane (MPCA), a methano-bridged pyrrolidine β-carboxylic acid, suggest an ordered secondary structure. Even in the absence of internal hydrogen bonding, solution NMR, X-ray, and in silico analyses of the tetramer are indicative of conformations with trans-amides and C(5)-amide-carbonyls oriented toward the C(4) bridgehead. This highly constrained β-amino acid could prove useful in the ongoing development of well-defined foldamers.2010-01-01T00:00:00Z2010 Dec2025-04-26T05:23:27.984Z2019-03-27T00:37:02ZS-EPMC29937842104344510.1021/ol1022917