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Volumn 75, Issue 3, 2010, Pages 772-782

From peptides to their alternating ester-urea analogues: Synthesis and influence of hydrogen bonding motif and stereochemistry on aggregation

Author keywords

[No Author keywords available]

Indexed keywords

AGGREGATION BEHAVIOR; CHEMICAL EQUATIONS; CONCENTRATION-DEPENDENT; EXPONENTIAL GROWTH; GELATORS; HYDROGEN BONDING MOTIFS; HYDROGEN BONDING SITES; MULTIVALENCY; NATURALLY OCCURRING; NMR SPECTROSCOPY; ORGANIC SOLUTIONS; PEPTIDE ASSOCIATION; PEPTIDE MIMICS; PEPTIDE SCAFFOLDS;

EID: 75749138516     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo902249w     Document Type: Article
Times cited : (8)

References (77)
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    • Elongation refers to the side chain repetition, i. e., the number of atoms in between neighboring monomer repeat units.
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    • Ureas have been used to facilitate aggregation and subsequent crystallization or gelation: (a) Desiraju, G. R., Crystal Engineering: The Design of Organic Solids; Elsevier: Amsterdam, The Netherlands, 1989;
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    • For related recent investigations, see: a, DOI: 10. 1021/ma902018w. Published Online: Oct 30
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    • See the Supporting Information
    • See the Supporting Information.
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    • 1H NMR chemical shifts remained constant, indicating the absence of intermolecular interaction, i. e., hydrogen bonds, and hence exclude aggregation.
    • 1H NMR chemical shifts remained constant, indicating the absence of intermolecular interaction, i. e., hydrogen bonds, and hence exclude aggregation.
  • 59
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    • Larger concentrations could hardly be realized as the solutions became rather viscous
    • Larger concentrations could hardly be realized as the solutions became rather viscous.
  • 60
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    • 3 was not used as an alternative solvent as the aggregation process should be pH-dependent.
    • 3 was not used as an alternative solvent as the aggregation process should be pH-dependent.
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    • This factor is based on the average chemical shift differences of all participating protons numbered in Figures 5-7, Due to the limited concentration range and the significant deviations of the chemical shift differences of the individual protons, no association constants were calculated as these individual or average values would have rather limited meaning. True association constants necessitate, for example, in depth isothermal titration calorimetry measurements
    • This factor is based on the average chemical shift differences of all participating protons (numbered in Figures 5-7). Due to the limited concentration range and the significant deviations of the chemical shift differences of the individual protons, no association constants were calculated as these individual or average values would have rather limited meaning. True association constants necessitate, for example, in depth isothermal titration calorimetry measurements.
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    • A theoretical treatment is given in: (c) Mammen, M.; Shaknovich, E. I.; Whitesides, G. M. J. Org. Chem. 1998, 63, 3168.
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    • and references cited therein. For a highlight, see
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* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.