Journal of the American Chemical Society
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Biofilm Formation and Potentiates β-Lactam Antibiotics and
Vancomycin in Resistant Strains of Staphylococcus aureus. ACS Infect.
Dis. 2019, 5, 1397–1410.
Newton for helpful discussions and assistance with the docking
studies. For insightful conversations and access to the Asp-peptide
library, we would like to thank Dr. Sheng-Ying Hsieh, Dr. Yu Tang
and Dr. Simone Crotti. For critical suggestions and assistance with
manuscript preparations, we thank Dr. Margaret Hilton, Dr.
Hyung Yoon, and Gavin Coombs.
5. Cuboni, S.; Devigny, C.; Hoogeland, B.; Strasser, A.; Pomplun,
S.; Hauger, B.; Höfner, G.; Wanner, K. T.; Eder, M.; Buschauer, A.;
Holsboer, F.; Hausch, F. Loratadine and Analogues: Discovery and
Preliminary Structure–Activity Relationship of Inhibitors of the Amino
Acid Transporter B0AT2. J. Med. Chem. 2014, 57, 9473–9479.
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West, R. E.; Williams, S. M.; Greenfeder, S.; Billah, M.; Kreutner, W.;
Egan, R. W. Biochemical characterization of desloratadine, a potent
antagonist of the human histamine H1 receptor. Eur. J. Pharmacol.
2002, 449, 229–237; (b) Canonica, G. W.; Blaiss, M. Antihistaminic,
anti-inflammatory, and antiallergic properties of the nonsedating
ABBREVIATIONS
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(a-Me)Pro: a-methyl-L-proline; Acpc: 1-aminocyclopropane car-
boxylic acid; Boc: tert -butoxycarbonyl; DIC: N,N’-diisopropyl-
carbodiimide; DKR: dynamic kinetic resolution; FLIPR: fluores-
cence imagine plate reader; GPCR: G-protein-coupled-receptor;
H-bond: hydrogen bond; H1R: human histamine H1 receptor; KR:
kinetic resolution; m-CPBA: meta-chloro-peroxybenzoic acid; Ts:
tosyl
second-generation antihistamine desloratadine:
evidence. World Allergy Organ. J 2011, 4, 47–53.
a review of the
7. (a) Clayden, J.; Moran, W. J.; Edwards, P. J.; LaPlante, S. R. The
Challenge of Atropisomerism in Drug Discovery. Angew. Chem. Int.
Ed. 2009, 48, 6398–6401; (b) LaPlante, S. R.; Fader, L. D.; Fandrick,
K. R.; Fandrick, D. R.; Hucke, O.; Kemper, R.; Miller, S. P. F.; Edwards,
P. J. Assessing Atropisomer Axial Chirality in Drug Discovery and De-
velopment. J. Med. Chem. 2011, 54, 7005–7022; (c) Kumarasamy, E.;
Raghunathan, R.; Sibi, M. P.; Sivaguru, J. Nonbiaryl and Heterobiaryl
Atropisomers: Molecular Templates with Promise for Atropselective
Chemical Transformations. Chem. Rev. 2015, 115, 11239–11300; (d)
Smyth, J. E.; Butler, N. M.; Keller, P. A. A twist of nature - the signifi-
cance of atropisomers in biological systems. Nat. Prod. Rep. 2015, 32,
1562–1583; (e) Glunz, P. W. Recent encounters with atropisomerism
in drug discovery. Bioorganic Med. Chem. Lett. 2018, 28, 53–60; (f)
Toenjes, S. T.; Gustafson, J. L. Atropisomerism in medicinal chemis-
try: challenges and opportunities. Future Med. Chem. 2018, 10, 409–
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pounds via Asymmetric Organocatalysis. Acc. Chem. Res. 2018, 51,
534–547; (h) Mancinelli, M.; Bencivenni, G.; Pecorari, D.; Mazzanti,
A. Stereochemistry and Recent Applications of Axially Chiral Organic
Molecules. Eur. J. Org. Chem., 2020, DOI: 10.1002/ejoc.201901918.
8. (a) Piwinski, J. J.; Wong, J. K.; Chan, T. M.; Green, M. J.; Ganguly,
A. K. Hydroxylated metabolites of loratadine: an example of
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C.; Chan, T.-M.; Motassim Billah, M.; Tozzi, S.; McPhail, A. T.
Conformational considerations in the design of dual antagonists of
platelet-activating factor (PAF) and histamine. Bioorganic Med.
Chem. 1999, 7, 1413–1423; (c) Morgan, B.; Zaks, A.; Dodds, D. R.;
Liu, J.; Jain, R.; Megati, S.; Njoroge, F. G.; Girijavallabhan, V. M.
Enzymatic Kinetic Resolution of Piperidine Atropisomers:ꢀ Synthesis
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