Crystal Structures of Dipeptides Derived from the β-Amino Acids (1R,2S)-2-Aminocyclopentanecarboxylic Acid and (1S,2R,3S)-2-Amino-3-methylcyclopentanecarboxylic Acid

被引:4
作者
Abraham, Elin [1 ]
Davies, Stephen G. [1 ]
Roberts, Paul M. [1 ]
Thompson, Amber L. [1 ]
Thomson, James E. [1 ]
机构
[1] Univ Oxford, Dept Chem, Chem Res Lab, Oxford OX1 3TA, England
关键词
beta-Peptides; beta-Sheet; Asymmetric synthesis; Lithium amide; Parallel kinetic resolution; PARALLEL KINETIC RESOLUTION; HELICAL SECONDARY STRUCTURE; X-RAY CRYSTALLOGRAPHY; DE-NOVO DESIGN; ASYMMETRIC-SYNTHESIS; BETA(2)-AMINO ACIDS; ABSOLUTE-STRUCTURE; AQUEOUS-SOLUTION; CHEMICAL-SHIFTS; PEPTIDES;
D O I
10.1007/s10870-011-0164-x
中图分类号
O7 [晶体学];
学科分类号
0702 ; 070205 ; 0703 ; 080501 ;
摘要
Crystals of the dimeric beta-peptides 13 and 20, derived from (1R,2S)-2-aminocyclopentanecarboxylic acid and (1S,2R,3S)-2-amino-3-methylcyclopentanecarboxylic acid, respectively, were synthesised and studied by X-ray diffraction in order to establish their solid state secondary structural characteristics. Compound 13 crystallises in the monoclinic space group P 2 (1) with cell parameters of a = 5.2682(1) , b = 9.1211(2) , c = 22.4467(6) , beta = 91.3855(9)A degrees, V = 1078.29(4) (3) and Z = 2. Compound 20 crystallizes in the orthorhombic space group P 2 (1) 2 (1) 2 (1) with cell parameters of a = 5.0968(1) , b = 11.5546(2) , c = 43.5414(8) , V = 2564.22(8) (3) and Z = 4. In both cases adjacent molecules are linked by a series of N-H center dot center dot center dot O=C hydrogen bonds to form beta-sheet like structures.
引用
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页码:1722 / 1728
页数:7
相关论文
共 55 条
[1]   Parallel kinetic resolution of methyl (RS)-5-tris(phenylthio)methyl-cyclopent-1-ene-carboxylate for the asymmetric synthesis of (1R,2S,5S)and (1S,2R,5R)-5-methyl-cispentacin [J].
Abraham, Elin ;
Davies, Stephen G. ;
Docherty, Alexander J. ;
Ling, Kenneth B. ;
Roberts, Paul M. ;
Russell, Angela J. ;
Thomson, James E. ;
Toms, Steven M. .
TETRAHEDRON-ASYMMETRY, 2008, 19 (11) :1356-1362
[2]   A systematic study of the solid state and solution phase conformational preferences of β-peptides derived from C(3)-alkyl substituted transpentacin derivatives [J].
Abraham, Elin ;
Claridge, Timothy D. W. ;
Davies, Stephen G. ;
Odell, Barbara ;
Roberts, Paul M. ;
Russell, Angela J. ;
Smith, Andrew D. ;
Smith, Lorna J. ;
Storr, Helen R. ;
Sweet, Miles J. ;
Thompson, Amber L. ;
Thomson, James E. ;
Tranter, George E. ;
Watkin, David J. .
TETRAHEDRON-ASYMMETRY, 2011, 22 (01) :69-100
[3]   A systematic study of the solid state and solution phase conformational preferences of β-peptides derived from transpentacin [J].
Abraham, Elin ;
Bailey, Callum W. ;
Claridge, Timothy D. W. ;
Davies, Stephen G. ;
Ling, Kenneth B. ;
Odell, Barbara ;
Rees, Thomas L. ;
Roberts, Paul M. ;
Russell, Angela J. ;
Smith, Andrew D. ;
Smith, Lorna J. ;
Storr, Helen R. ;
Sweet, Miles J. ;
Thompson, Amber L. ;
Thomson, James E. ;
Tranter, George E. ;
Watkin, David J. .
TETRAHEDRON-ASYMMETRY, 2010, 21 (13-14) :1797-1815
[4]   β-Amino acid-containing hybrid peptides -: new opportunities in peptidomimetics [J].
Aguilar, Marie-Isabel ;
Purcell, Anthony W. ;
Devi, Romila ;
Lew, Rebecca ;
Rossjohn, Jamie ;
Smitha, A. Ian ;
Perlmutter, Patrick .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2007, 5 (18) :2884-2890
[5]   SIR92 - a program for automatic solution of crystal structures by direct methods [J].
ALTOMARE, A ;
CASCARANO, G ;
GIACOVAZZO, G ;
GUAGLIARDI, A ;
BURLA, MC ;
POLIDORI, G ;
CAMALLI, M .
JOURNAL OF APPLIED CRYSTALLOGRAPHY, 1994, 27 :435-435
[6]   Residue-based control of helix shape in beta-peptide oligomers [J].
Appella, DH ;
Christianson, LA ;
Klein, DA ;
Powell, DR ;
Huang, XL ;
Barchi, JJ ;
Gellman, SH .
NATURE, 1997, 387 (6631) :381-384
[7]   beta-peptide foldamers: Robust Helix formation in a new family of beta-amino acid oligomers [J].
Appella, DH ;
Christianson, LA ;
Karle, IL ;
Powell, DR ;
Gellman, SH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (51) :13071-13072
[8]   Theoretical and experimental circular dichroic spectra of the novel helical foldamer poly[(1R,2R)-trans-2-aminocyclopentanecarboxylic acid] [J].
Applequist, J ;
Bode, KA ;
Appella, DH ;
Christianson, LA ;
Gellman, SH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (19) :4891-4892
[9]   Parallel kinetic resolution of tert-butyl (RS)-3-oxy-substituted cyclopent-1-ene-carboxylates for the asymmetric synthesis of 3-oxy-substituted cispentacin and transpentacin derivatives [J].
Aye, Yimon ;
Davies, Stephen G. ;
Garner, A. Christopher ;
Roberts, Paul M. ;
Smith, Andrew D. ;
Thomson, James E. .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2008, 6 (12) :2195-2203
[10]   Solution conformations of helix-forming β-amino acid homooligomers [J].
Barchi, JJ ;
Huang, XL ;
Appella, DH ;
Christianson, LA ;
Durell, SR ;
Gellman, SH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (12) :2711-2718