Synthesis of small cyclic peptides via reverse turn induced ring closing metathesis of tripeptides

Journal of Organic Chemistry

Volumn 67, Issue 23, 2002, Pages 8247-8250

  Prabhakaran, E N ^a   Rao, I Nageswara ^b   Boruah, Anima ^b   Iqbal, Javed ^a,b,c  

^a INDIAN INSTITUTE OF TECHNOLOGY KANPUR   (India)

^b DR REDDY'S LABORATORIES LTD   (India)

^c REGIONAL RESEARCH LABORATORY CSIR   (India)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLIZATION;

CONFORMATIONS; SYNTHESIS (CHEMICAL);

AMINO ACIDS;

PROTEINASE INHIBITOR; TRIPEPTIDE; CYCLOPEPTIDE; OLIGOPEPTIDE;

ARTICLE; CATALYSIS; CONFORMATIONAL TRANSITION; CYCLIZATION; HUMAN IMMUNODEFICIENCY VIRUS; RING CLOSING METATHESIS; STRUCTURE ANALYSIS; SYNTHESIS; CHEMICAL STRUCTURE; CHEMISTRY; CIRCULAR DICHROISM; HYDROGEN BOND; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PROTEIN SECONDARY STRUCTURE;

CIRCULAR DICHROISM; CYCLIZATION; HYDROGEN BONDING; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, MOLECULAR; OLIGOPEPTIDES; PEPTIDES, CYCLIC; PROTEIN STRUCTURE, SECONDARY;

EID: 0037111713     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0200320     Document Type: Article

References (22)

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22. 2 workstation. Charges were calculated by using the charge-equilibration method. The CFF9 force field with default parameters was used throughout the simulations. To understand the conformational freedom, simulated annealing molecular dynamics calculations were carried out. The temperature was varied between 300 and 1200 K in steps of 50 K for 100/150 cycles. The molecules were allowed to equilibrate for 0.5 ps for every change in temperature. Minimizations were done first with steepest descent, followed by conjugate gradient methods for a maximum of 1000 iterations each or a root-mean-square deviation of 0.01 kcal/mol, whichever was earlier. The energy- minimized structures were then subjected to MD simulations. Various conformers obtained in each MD run were minimized by using the above-mentioned minimization protocol. The energy difference between the lowest energy conformer and the next higher energy conformer was 5.6 kcal/mol for 1c and 8.35 kcal/mol for 2c.