BIOMAT Database Logo BIOMAT Database Logo

Structure of N-tert-butoxycarbonyl-L-phenylalanine benzyl ester. 1992

M Gikas, and G Agelis, and J Matsoukas, and G J Moore, and L Dupont, and S Englebert
Department of Chemistry, University of Patras, Greece.

C21H25NO4, Mr = 355.4, monoclinic, P2(1), a = 5.206 (2), b = 17.294 (4), c = 10.972 (2) A, beta = 98.91 (1) degrees, V = 976 (1) A3, Z = 2, Dx = 1.21 Mg m-3, lambda(Cu K alpha) = 1.5418 A, mu = 0.68 mm-1, F(000) = 380, T = 293 K, final R = 0.071 for 1186 observed reflections. The structure is stabilized in the a direction by means of intermolecular hydrogen bonds [N(1) ... O(2i) = 3.01 (1) A, (i) = x + 1, y, z]. The urethane amide bond adopts the trans conformation [H(1)-N(1)-C(5) = O(2) = 169 (3) degrees]. The butoxycarbonyl (Boc) moiety is directed away from both the phenylalanine aromatic ring and the benzyl ester ring, in contrast to the arrangement observed in Bocphenylalanine phenacyl ester [Vlassi, Germain, Matsoukas, Psachoulia, Voliotis & Leban (1987). Acta Cryst. C43, 2173-2175]. The orientation assumed by the Boc group may be the result of steric restrictions imposed by both rings.

UI MeSH Term Description Entries
D008956 Models, Chemical Theoretical representations that simulate the behavior or activity of chemical processes or phenomena; includes the use of mathematical equations, computers, and other electronic equipment. Chemical Models,Chemical Model,Model, Chemical
D008968 Molecular Conformation The characteristic three-dimensional shape of a molecule. Molecular Configuration,3D Molecular Structure,Configuration, Molecular,Molecular Structure, Three Dimensional,Three Dimensional Molecular Structure,3D Molecular Structures,Configurations, Molecular,Conformation, Molecular,Conformations, Molecular,Molecular Configurations,Molecular Conformations,Molecular Structure, 3D,Molecular Structures, 3D,Structure, 3D Molecular,Structures, 3D Molecular
D010649 Phenylalanine An essential aromatic amino acid that is a precursor of MELANIN; DOPAMINE; noradrenalin (NOREPINEPHRINE), and THYROXINE. Endorphenyl,L-Phenylalanine,Phenylalanine, L-Isomer,L-Isomer Phenylalanine,Phenylalanine, L Isomer
D003460 Crystallization The formation of crystalline substances from solutions or melts. (McGraw-Hill Dictionary of Scientific and Technical Terms, 4th ed) Crystalline Polymorphs,Polymorphism, Crystallization,Crystal Growth,Polymorphic Crystals,Crystal, Polymorphic,Crystalline Polymorph,Crystallization Polymorphism,Crystallization Polymorphisms,Crystals, Polymorphic,Growth, Crystal,Polymorph, Crystalline,Polymorphic Crystal,Polymorphisms, Crystallization,Polymorphs, Crystalline
D014961 X-Ray Diffraction The scattering of x-rays by matter, especially crystals, with accompanying variation in intensity due to interference effects. Analysis of the crystal structure of materials is performed by passing x-rays through them and registering the diffraction image of the rays (CRYSTALLOGRAPHY, X-RAY). (From McGraw-Hill Dictionary of Scientific and Technical Terms, 4th ed) Xray Diffraction,Diffraction, X-Ray,Diffraction, Xray,Diffractions, X-Ray,Diffractions, Xray,X Ray Diffraction,X-Ray Diffractions,Xray Diffractions

Related Publications

M Gikas, and G Agelis, and J Matsoukas, and G J Moore, and L Dupont, and S Englebert
O-Benzyl-N-tert-butoxycarbonyl-N-methyl-L-tyrosine.
June 2002, Acta crystallographica. Section C, Crystal structure communications,
M Gikas, and G Agelis, and J Matsoukas, and G J Moore, and L Dupont, and S Englebert
Benzyl tert-butoxycarbonyl-alpha-aminoisobutyrate.
April 2001, Acta crystallographica. Section C, Crystal structure communications,
M Gikas, and G Agelis, and J Matsoukas, and G J Moore, and L Dupont, and S Englebert
Characteristic molecular packing in the crystal structure of tert-butoxycarbonyl-L-phenylalanyl-L-methionine methyl ester.
December 1994, International journal of peptide and protein research,
M Gikas, and G Agelis, and J Matsoukas, and G J Moore, and L Dupont, and S Englebert
N-(tert-butoxycarbonyl)-L-valyl-L-valine methyl ester: a twisted parallel β-sheet in the crystal structure of a protected dipeptide.
August 2011, Acta crystallographica. Section C, Crystal structure communications,
M Gikas, and G Agelis, and J Matsoukas, and G J Moore, and L Dupont, and S Englebert
An efficient synthesis of N-tert-butoxycarbonyl-O-cyclohexyl-L-tyrosine.
February 2001, Chemical & pharmaceutical bulletin,
M Gikas, and G Agelis, and J Matsoukas, and G J Moore, and L Dupont, and S Englebert
N-(tert-butoxycarbonyl)-O-allyl-L-seryl-α-aminoisobutyryl-L-valine methyl ester: a protected tripeptide with an allylated serine residue.
September 2011, Acta crystallographica. Section C, Crystal structure communications,
M Gikas, and G Agelis, and J Matsoukas, and G J Moore, and L Dupont, and S Englebert
N-carboxy-L-aspartic anhydride benzyl ester.
March 2003, Acta crystallographica. Section C, Crystal structure communications,
M Gikas, and G Agelis, and J Matsoukas, and G J Moore, and L Dupont, and S Englebert
Pseudopolymorphism of N-acetyl-L-phenylalanine methyl ester.
April 2008, Acta crystallographica. Section B, Structural science,
M Gikas, and G Agelis, and J Matsoukas, and G J Moore, and L Dupont, and S Englebert
Peptide conformations. Crystal structures of tert-butyloxycarbonylglycyl-L-proline and its benzyl ester.
February 1977, Journal of the American Chemical Society,
M Gikas, and G Agelis, and J Matsoukas, and G J Moore, and L Dupont, and S Englebert
Synthesis and biological evaluation of N-(carbobenzyloxy)-l-phenylalanine and N-(carbobenzyloxy)-l-aspartic acid-β-benzyl ester derivatives as potent topoisomerase IIα inhibitors.
June 2017, Bioorganic & medicinal chemistry,
Copied contents to your clipboard!