Helical Structures of Cyclopentene-based α,α-Disubstituted α-Amino Acid Homopeptides

被引:1
作者
Tanaka, Masakazu [1 ]
Yakabi, Haruka [2 ]
Nakatani, Haruki [2 ]
Ueda, Atsushi [1 ]
Doi, Mitsunobu [3 ]
Oba, Makoto [1 ]
机构
[1] Nagasaki Univ, Grad Sch Biomed Sci, 1-14 Bunkyo Machi, Nagasaki 8528521, Japan
[2] Nagasaki Univ, Sch Pharmaceut Sci, 1-14 Bunkyo Machi, Nagasaki 8528521, Japan
[3] Osaka Univ Pharmaceut Sci, Osaka 5691094, Japan
关键词
Conformation; Cyclopentene; alpha; alpha-Disubstituted alpha-amino acid; Helix; Peptide; X-RAY-DIFFRACTION; STEREOSELECTIVE-SYNTHESIS; C-ALPHA; ALPHA-DIALKYLATED GLYCINES; DIALKYLATED GLYCINES; PEPTIDES; VERSATILITY; CONFORMATION; ABSORPTION; HANDEDNESS; H-1-NMR;
D O I
10.2533/chimia.2018.848
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The cyclopentene-based alpha,alpha-disubstituted alpha-amino acid Ac(5)c(=) and its homopeptides, up to nona-peptides, were synthesized. The side-chain cyclopentene was expected to become symmetric, the C-alpha-carbon to be puckered, and other C-beta, C-beta', C-gamma'-carbons to be coplanar. As expected, side-chain cyclopentene conformations became symmetric and Cu-carbons were puckered. Conformational studies using FT-IR absorption, H-1 NMR spectra, and X-ray crystallographic analyses revealed that Ac(5)c(=) homopeptides did not form a planar conformation, but assumed a 3(10)-helical structure, similar to cyclopentane-based alpha,alpha-disubstituted a-amino acid homopeptides.
引用
收藏
页码:848 / 852
页数:5
相关论文
共 31 条
[1]   Helical Structures of Bicyclic α-Amino Acid Homochiral Oligomers with the Stereogenic Centers at the Side-Chain Fused-Ring Junctions [J].
Anan, Kosuke ;
Demizu, Yosuke ;
Oba, Makoto ;
Kurihara, Masaaki ;
Doi, Mitsunobu ;
Suemune, Hiroshi ;
Tanaka, Masakazu .
HELVETICA CHIMICA ACTA, 2012, 95 (10) :1694-1713
[2]   STRUCTURAL VERSATILITY OF PEPTIDES FROM C-ALPHA-ALPHA-DIALKYLATED GLYCINES .1. A CONFORMATIONAL ENERGY COMPUTATION AND X-RAY-DIFFRACTION STUDY OF HOMO-PEPTIDES FROM C-ALPHA-ALPHA-DIETHYLGLYCINE [J].
BENEDETTI, E ;
BARONE, V ;
BAVOSO, A ;
DIBLASIO, B ;
LELJ, F ;
PAVONE, V ;
PEDONE, C ;
BONORA, GM ;
TONIOLO, C ;
LEPLAWY, MT ;
KACZMAREK, K ;
REDLINSKI, A .
BIOPOLYMERS, 1988, 27 (03) :357-371
[3]  
Benedetti E, 1996, BIOPOLYMERS, V40, P3, DOI 10.1002/(SICI)1097-0282(1996)40:1<3::AID-BIP2>3.0.CO
[4]  
2-#
[5]   Stereoselective synthesis of quaternary α-amino acids.: Part 2.: Cyclic compounds [J].
Cativiela, C ;
Díaz-de-Villegas, MD .
TETRAHEDRON-ASYMMETRY, 2000, 11 (03) :645-732
[6]   Stereoselective synthesis of quaternary α-amino acids.: Part 1:: Acyclic compounds [J].
Cativiela, C ;
Diaz-de-Villegas, MD .
TETRAHEDRON-ASYMMETRY, 1998, 9 (20) :3517-3599
[7]   Recent progress on the stereoselective synthesis of cyclic quaternary α-amino acids [J].
Cativiela, Carlos ;
Ordonez, Mario .
TETRAHEDRON-ASYMMETRY, 2009, 20 (01) :1-63
[8]   STRUCTURAL VERSATILITY OF PEPTIDES FROM C-ALPHA,ALPHA-DIALKYLATED GLYCINES - AN INFRARED-ABSORPTION AND H-1-NMR STUDY OF HOMOPEPTIDES FROM 1-AMINOCYCLOPENTANE-1-CARBOXYLIC ACID [J].
CRISMA, M ;
BONORA, GM ;
TONIOLO, C ;
BENEDETTI, E ;
BAVOSO, A ;
DIBLASIO, B ;
PAVONE, V ;
PEDONE, C .
INTERNATIONAL JOURNAL OF BIOLOGICAL MACROMOLECULES, 1988, 10 (05) :300-304
[9]   Handedness preference and switching of peptide helices. Part II: Helices based on noncoded α-amino acids [J].
Crisma, Marco ;
De Zotti, Marta ;
Formaggio, Fernando ;
Peggion, Cristina ;
Moretto, Alessandro ;
Toniolo, Claudio .
JOURNAL OF PEPTIDE SCIENCE, 2015, 21 (03) :148-177
[10]  
Ehrlich F, 1908, BIOCHEM Z, V8, P438