Biomaterial Database

Conformational study of eight-membered diazocine turn mimics by two-dimensional NMR spectroscopy. 1994

J W Bean, and J Briand, and J L Burgess, and J F Callahan

Department of Physical & Structural Chemistry, SmithKline Beecham Pharmaceuticals, King of Prussia, PA 19406-0939.

The eight-membered ring conformations of two diazocine turn mimics, methyl-[2,5-dioxo-3-(S)-(3-omega-tosyl-guanidino-propyl)-4-methyl-octahy dro- 1,4-diazocin-1-yl]acetate (I) and methyl-[2,5-dioxo-3-(S)-(3-omega-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.

UI	MeSH Term	Description	Entries
D008958	Models, Molecular	Models used experimentally or theoretically to study molecular shape, electronic properties, or interactions; includes analogous molecules, computer-generated graphics, and mechanical structures.	Molecular Models,Model, Molecular,Molecular Model
D009682	Magnetic Resonance Spectroscopy	Spectroscopic method of measuring the magnetic moment of elementary particles such as atomic nuclei, protons or electrons. It is employed in clinical applications such as NMR Tomography (MAGNETIC RESONANCE IMAGING).	In Vivo NMR Spectroscopy,MR Spectroscopy,Magnetic Resonance,NMR Spectroscopy,NMR Spectroscopy, In Vivo,Nuclear Magnetic Resonance,Spectroscopy, Magnetic Resonance,Spectroscopy, NMR,Spectroscopy, Nuclear Magnetic Resonance,Magnetic Resonance Spectroscopies,Magnetic Resonance, Nuclear,NMR Spectroscopies,Resonance Spectroscopy, Magnetic,Resonance, Magnetic,Resonance, Nuclear Magnetic,Spectroscopies, NMR,Spectroscopy, MR
D009842	Oligopeptides	Peptides composed of between two and twelve amino acids.	Oligopeptide
D011487	Protein Conformation	The characteristic 3-dimensional shape of a protein, including the secondary, supersecondary (motifs), tertiary (domains) and quaternary structure of the peptide chain. PROTEIN STRUCTURE, QUATERNARY describes the conformation assumed by multimeric proteins (aggregates of more than one polypeptide chain).	Conformation, Protein,Conformations, Protein,Protein Conformations
D001392	Azocines
D015394	Molecular Structure	The location of the atoms, groups or ions relative to one another in a molecule, as well as the number, type and location of covalent bonds.	Structure, Molecular,Molecular Structures,Structures, Molecular