Conformational study of eight‐membered diazocine turn mimics by two‐dimensional NMR spectroscopy

FEBS Letters

Burgess, Joelle L.¹  Briand, Jacques¹  Bean, John W.¹  Callahan, James F.¹ 

[1] Departments of Physical & Structural Chemistry and Medicinal Chemistry, SmithKline Beecham Pharmaceuticals, Mail Code UW-2940, PO Box 1539, King of Prussia, PA 19406-0939, USA

关键词: NMR;    Coupling constant;    Conformational mimetics;    Arg-Gly-Asp (RGD) peptide;    Molecular modeling;    NMR;    nuclear magnetic resonance spectroscopy;    TOCSY;    total correlation spectroscopy;    ROESY;    rotating frame nuclear Overhauser enhancement spectroscopy;    P.E.COSY;    primitive exclusive correlation spectroscopy;   

DOI  :  10.1016/0014-5793(94)01106-0

学科分类：生物化学/生物物理

来源: John Wiley & Sons Ltd.

【 摘 要 】

The eight-membered ring conformations of two diazocine turn mimics, methyl-[2,5-dioxo-3-(S)-(3-ω-tosyl-guanidino-propyl)-4-methyl-octahydro-1,4-diazocin-1-yl]acetate (I) and methyl-[2,5-dioxo-3-(S)-(3-ω-tosyl-guanidino-propyl)-octahydro-1,4-diazocin-1-yl]acetate (II), were determined using torsion angle constraints derived from ³J(C,H) coupling constants extracted from ¹³C-filtered TOCSY spectra with ¹³C in natural abundance. For I, the torsion angle constraints derived from ³J(C,H) coupling constants were in agreement with torsion angle constraints derived from ³J(H,H) coupling constants extracted from a P.E.COSY spectrum. Similar ³J(C,H) coupling constants were found for I and II, and they shared an identical eight-membered ring conformation characterized by two cis-amide bonds and a staggered conformation of the trimethylene group in which the H3 proton is proximal to both the H6 and H8 protons.

【 授权许可】

Unknown