DETERMINATION OF **3J//H//F AND **4J//H//F KARPLUS RELATIONSHIPS FOR THE phi AND PSI ANGLES OF PEPTIDES USING N-FLUOROAMIDES AS MODELS.

Charles F. Hammer, Srinivasan Chandrasegaran

Research output: Contribution to journalArticle

Abstract

A series of N-fluoroamide derivatives were synthesized by the reaction of CF//3OF with the corresponding amides. The reaction procedure of Barton et al. was appropriately modified to maximize the yield of the pure monofluoro derivatives. The compounds were examined as models for the determination of the phi prime (**3J//H//F) and PSI prime (**4J//H**F) angles of peptides with **1H, **1**9F, and **1**3C NMR spectroscopy. Investigation of this series of compounds has led to Karplus-type relations between phi prime vs. **3J//H**F and PSI vs. **4J//H**F using the experimental coupling constants. As the signs of the coupling constants could not be determined at this time, several possibilities arise for these relations.

Original languageEnglish (US)
Pages (from-to)1543-1552
Number of pages10
JournalJournal of the American Chemical Society
Volume106
Issue number6
StatePublished - Jan 1 1984

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Amides
Peptides
Magnetic Resonance Spectroscopy
Lead compounds
Derivatives
Nuclear magnetic resonance spectroscopy
F-chemotactic peptide
benzyloxycarbonyl-isoleucyl-glutamyl(O-tert-butyl)-alanyl-leucinal

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

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title = "DETERMINATION OF **3J//H//F AND **4J//H//F KARPLUS RELATIONSHIPS FOR THE phi AND PSI ANGLES OF PEPTIDES USING N-FLUOROAMIDES AS MODELS.",
abstract = "A series of N-fluoroamide derivatives were synthesized by the reaction of CF//3OF with the corresponding amides. The reaction procedure of Barton et al. was appropriately modified to maximize the yield of the pure monofluoro derivatives. The compounds were examined as models for the determination of the phi prime (**3J//H//F) and PSI prime (**4J//H**F) angles of peptides with **1H, **1**9F, and **1**3C NMR spectroscopy. Investigation of this series of compounds has led to Karplus-type relations between phi prime vs. **3J//H**F and PSI vs. **4J//H**F using the experimental coupling constants. As the signs of the coupling constants could not be determined at this time, several possibilities arise for these relations.",
author = "Hammer, {Charles F.} and Srinivasan Chandrasegaran",
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T1 - DETERMINATION OF **3J//H//F AND **4J//H//F KARPLUS RELATIONSHIPS FOR THE phi AND PSI ANGLES OF PEPTIDES USING N-FLUOROAMIDES AS MODELS.

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AU - Chandrasegaran, Srinivasan

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N2 - A series of N-fluoroamide derivatives were synthesized by the reaction of CF//3OF with the corresponding amides. The reaction procedure of Barton et al. was appropriately modified to maximize the yield of the pure monofluoro derivatives. The compounds were examined as models for the determination of the phi prime (**3J//H//F) and PSI prime (**4J//H**F) angles of peptides with **1H, **1**9F, and **1**3C NMR spectroscopy. Investigation of this series of compounds has led to Karplus-type relations between phi prime vs. **3J//H**F and PSI vs. **4J//H**F using the experimental coupling constants. As the signs of the coupling constants could not be determined at this time, several possibilities arise for these relations.

AB - A series of N-fluoroamide derivatives were synthesized by the reaction of CF//3OF with the corresponding amides. The reaction procedure of Barton et al. was appropriately modified to maximize the yield of the pure monofluoro derivatives. The compounds were examined as models for the determination of the phi prime (**3J//H//F) and PSI prime (**4J//H**F) angles of peptides with **1H, **1**9F, and **1**3C NMR spectroscopy. Investigation of this series of compounds has led to Karplus-type relations between phi prime vs. **3J//H**F and PSI vs. **4J//H**F using the experimental coupling constants. As the signs of the coupling constants could not be determined at this time, several possibilities arise for these relations.

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