메뉴 건너뛰기




Volumn 37, Issue 1, 2009, Pages 11-25

A new mathematical equation relating activation energy to bond angle and distance: A key for understanding the role of acceleration in lactonization of the trimethyl lock system

Author keywords

Hydroxy acids; Lactonization; Proximity orientation; Stereopopulation control; Steric effects; Tri methyl effect

Indexed keywords

CARBON; CARBONYL DERIVATIVE; ETHER; HYDROXYACID; HYDROXYHYDROCINNAMIC ACID DERIVATIVE; HYDROXYL GROUP; LACTONE DERIVATIVE; OXYGEN; UNCLASSIFIED DRUG;

EID: 58549095423     PISSN: 00452068     EISSN: 10902120     Source Type: Journal    
DOI: 10.1016/j.bioorg.2008.08.006     Document Type: Article
Times cited : (31)

References (81)
  • 6
    • 58549088519 scopus 로고    scopus 로고
    • M.I. Page (Ed.) The Chemistry of Enzyme Action, Elsevier, Amsterdam, 1984.
    • M.I. Page (Ed.) The Chemistry of Enzyme Action, Elsevier, Amsterdam, 1984.
  • 7
    • 85042336834 scopus 로고
    • Gandour R.D., and Schowen R.L. (Eds), Plenum Press, New York
    • In: Gandour R.D., and Schowen R.L. (Eds). Transition States of Biochemical Processes (1978), Plenum Press, New York
    • (1978) Transition States of Biochemical Processes
  • 34
    • 28544453067 scopus 로고    scopus 로고
    • and references therein
    • Menger F.M. Pure Appl. Chem. 77 (2005) 1873 and references therein
    • (2005) Pure Appl. Chem. , vol.77 , pp. 1873
    • Menger, F.M.1
  • 45
    • 58549102942 scopus 로고    scopus 로고
    • R. Karaman, Presented in part at the First International Conference on Drug Design and Discovery in Dubai, UAE, February 4-7, 2008
    • R. Karaman, Presented in part at the First International Conference on Drug Design and Discovery in Dubai, UAE, February 4-7, 2008
  • 47
    • 58549097478 scopus 로고    scopus 로고
    • R. Karaman, Tetrahedron Lett., accepted for publication.
    • R. Karaman, Tetrahedron Lett., accepted for publication.
  • 54
    • 58549110468 scopus 로고    scopus 로고
    • Available from: .
    • Available from: .
  • 68
    • 0000274829 scopus 로고
    • and references cited therein
    • Li Y.Z., and Schuster G.B. J. Org. Chem. 53 (1988) 1273 and references cited therein
    • (1988) J. Org. Chem. , vol.53 , pp. 1273
    • Li, Y.Z.1    Schuster, G.B.2
  • 74
    • 58549090528 scopus 로고    scopus 로고
    • For details of crystal structure analysis, see Ref. [26].
    • For details of crystal structure analysis, see Ref. [26].
  • 75
    • 20044390256 scopus 로고    scopus 로고
    • For recent review on a gem- dimethyl effect see
    • For recent review on a gem- dimethyl effect see. Jung M.E., and Plizzi G. Chem. Rev. 105 (2005) 1735
    • (2005) Chem. Rev. , vol.105 , pp. 1735
    • Jung, M.E.1    Plizzi, G.2
  • 80
    • 58549085233 scopus 로고    scopus 로고
    • note
    • A reaction method was used to calculate the enthalpic and entropic changes in the second step in the approach of the phenolic oxygen onto the carboxylic carbon. A distance of O10-C1 was decreased in increments of 0.1 Å and was kept constant while full optimization of other parameters was calculated. The monitoring results clearly indicate that the change in entropy along the reaction pathway is negligible and that the change in free energy is mainly composed of enthalpic forces.
  • 81
    • 58549090740 scopus 로고    scopus 로고
    • note
    • A rotation of the carboxylic moiety around C2-C3 bond in 1a and 1c was conducted using a reaction coordinate method. This was accomplished by changing the dihedral angle O10C1C2C3 in increments of 36° while keeping the C1-O10 distance constant (2.0, 1.9 or 1.8 Å). The calculations indicate a higher barrier of rotation for 1a over 1c.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.