Non coded C alpha, alpha-disubstituted amino acids. X-ray diffraction analysis of a dipeptide containing (S)-alpha-methylserine(161 visite) Pavone V, Di Blasio B, Lombardi A, Maglio O, Isernia C, Pedone C, Benedetti E, Altmann E, Mutter M
Int J Pept Protein Res (ISSN: 0367-8377, 0367-8377print, 0367-8377linking), 1993 Jan; 41(1): 15-20.
Tipo di articolo: Journal Article, Research Support, Non-U. S. Gov'T,
Parole chiave: Alpha Methylserine, Dipeptide, Unclassified Drug, Article, Crystal Structure, Nonhuman, Protein Structure, X Ray Analysis, Crystallization, Hydrogen Bonding, Isomerism, Models, Molecular, Molecular Conformation, Support, Non-U.S. Gov, X-Ray Diffraction, Non-U. S. Gov, Chemistry, Analogs, Derivatives,
Affiliazioni:
Biocrystallographic Ctr. of the CNR, Department of Chemistry, University of Naples, Via Mezzocannone 4, 80134 Naples, Italy
Riferimenti:
Non disponibile.
The crystal and molecular structure of the fully protected dipeptide Boc-Val-(S)-alpha-MeSer-OMe has been determined by X-ray diffraction techniques. Crystals grown from ethyl acetate/n-pentane mixtures are tetragonal, space group I4(1), with cell parameters at 295 K of a = 15.307(2), c = 18.937(10)A, V = 4437.1A3, M.W. = 332.40, Z = 8, Dm = 0.99 g/cm3 and Dx = 0.995 g/cm3. The structure was solved by application of direct methods and refined to an R value of 0.028 for 1773 reflections with I > or = 3 sigma (I) collected on a CAD-4 diffractometer. Both chiral centers have the (S) configuration. The dipeptide assumes in the solid state an S shape. The urethane moiety is in the cis conformation, while the amide bond is in the common trans conformation. The conformational angles phi 1, psi 1 of the Val and phi 2, and psi 2 of the (S)-alpha MeSer fall in the F region of the phi-psi map. The isopropyl side chain of the Val residue has the (t, g-) conformation, while the Ser side chain has a g+ conformation. The hydrogen bond donor groups are all involved in intermolecular H-bond interactions. Along the quaternary axis the dipeptide molecules are linked to each other with the formation of infinite rows.
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