TY - JOUR
T1 - Water-Soluble Chiral Cyclic Peptoids and Their Sodium and Gadolinium Complexes
T2 - Study of Conformational and Relaxometric Properties
AU - D'Amato, Assunta
AU - Jiang, Linhai
AU - Della Sala, Giorgio
AU - Kirshenbaum, Kent
AU - Costabile, Chiara
AU - Furlan, Chiara
AU - Gianolio, Eliana
AU - Izzo, Irene
AU - De Riccardis, Francesco
N1 - Funding Information:
Financial support from the University of Salerno (FARB) and from PRIN 2020: “Natural Products-Assisted Organic Synthesis” (2020AEX4TA). This study was also supported by Grant CHE-2002890 from the National Science Foundation (U.S. National Science Foundation, to K.K.). The authors acknowledge the contribution of the X-ray facility at New York University’s Materials Research Science and Engineering Center (MRSEC) program under NSF Grants DMR-0820341 and DMR-1420073. L.J. gratefully acknowledges the New York University Chemistry Department for the Margaret and Herman Sokol Fellowship. The authors thank Dr. Chunhua Tony Hu (NYU Chemistry) for determining the X-ray crystal structure of the potassium complex of 1 . The authors thank Dr. Patrizia Iannece, University of Salerno, for HR-MS and Dr. Patrizia Oliva, University of Salerno, for NMR spectra.
Publisher Copyright:
© 2023 American Chemical Society. All rights reserved.
PY - 2023/6/2
Y1 - 2023/6/2
N2 - Cyclic peptoids are macrocyclic oligomers of N-substituted glycines with specific folding abilities and excellent metal binding properties. In this work, we show how strategic positioning of chiral (S)- and (R)-(1-carboxyethyl)glycine units influences the conformational stability of water-soluble macrocyclic peptoids as sodium complexes. The reported results are based on nuclear magnetic resonance spectroscopy, extensive computational studies, and X-ray diffraction analysis using single crystals grown from aqueous solutions. The studies include1H relaxometric investigations of hexameric cyclic peptoids in the presence of the Gd3+ion to assess their thermodynamic stabilities and relaxivities.
AB - Cyclic peptoids are macrocyclic oligomers of N-substituted glycines with specific folding abilities and excellent metal binding properties. In this work, we show how strategic positioning of chiral (S)- and (R)-(1-carboxyethyl)glycine units influences the conformational stability of water-soluble macrocyclic peptoids as sodium complexes. The reported results are based on nuclear magnetic resonance spectroscopy, extensive computational studies, and X-ray diffraction analysis using single crystals grown from aqueous solutions. The studies include1H relaxometric investigations of hexameric cyclic peptoids in the presence of the Gd3+ion to assess their thermodynamic stabilities and relaxivities.
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U2 - 10.1021/acs.joc.2c02713
DO - 10.1021/acs.joc.2c02713
M3 - Article
AN - SCOPUS:85159629778
SN - 0022-3263
VL - 88
SP - 6588
EP - 6598
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 11
ER -