Intramolecular hydrogen bond-controlled prolyl amide isomerization in glucosyl 3′(S)-hydroxy-5′-hydroxymethylproline hybrids: Influence of a C-5′-hydroxymethyl substituent on the thermodynamics and kinetics of prolyl amide cis/trans isomerization

Journal of Organic Chemistry

Volumn 74, Issue 10, 2009, Pages 3735-3743

  Zhang, Kaidong ^a   Teklebrhan, Robel B ^a   Schreckenbach, G ^a   Wetmore, Stacey ^b   Schweizer, Frank ^a  

^a UNIVERSITY OF MANITOBA   (Canada)

^b UNIVERSITY OF LETHBRIDGE   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

[CARBONYL; ACETYL GROUPS; CHEMICAL EQUATIONS; CIS ISOMERS; CIS/TRANS ISOMERIZATION; CIS/TRANS ISOMERS; COMPUTATIONAL CALCULATIONS; DFT CALCULATION; DIASTEREOISOMER; DIASTEREOISOMERS; HYDROXYMETHYL GROUPS; INTRAMOLECULAR HYDROGEN BOND; KINETIC PROPERTIES; LONE PAIR; MAGNETIZATION TRANSFER; NITROGEN ATOM; PEPTIDE MIMICS; PYRROLIDINE RINGS; TEMPERATURE COEFFICIENT; THERMODYNAMICS AND KINETICS; TRANS ISOMERS; TRANSITION STATE;

AMIDES; AMINES; BINDING SITES; ELECTRON TRANSITIONS; ESTERIFICATION; ESTERS; HYDROGEN; ISOMERIZATION; ISOMERS; METHANOL; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STEREOCHEMISTRY; SULFUR COMPOUNDS;

HYDROGEN BONDS;

GLUCOSYL (3' HYDROXY 5' HYDROXYMETHYL)PROLINE; PROLINE DERIVATIVE; PYRAN DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CARBOXY TERMINAL SEQUENCE; DIASTEREOISOMER; HYDROGEN BOND; ISOMERIZATION; KINETICS; MOLECULAR INTERACTION; THERMODYNAMICS;

AMIDES; BIOMIMETIC MATERIALS; DEUTERIUM OXIDE; HYDROGEN BONDING; HYDROXYPROLINE; KINETICS; MOLECULAR CONFORMATION; PEPTIDES; QUANTUM THEORY; SPECTROSCOPY, FOURIER TRANSFORM INFRARED; STEREOISOMERISM; TEMPERATURE; THERMODYNAMICS;

EID: 65949111068     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9003458     Document Type: Article

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