The vicinal F-C-C-F moiety as a tool for influencing peptide conformation

被引:46
作者
Schüler, M
O'Hagan, D [1 ]
Slawin, AMZ
机构
[1] Univ St Andrews, Sch Chem, St Andrews KY16 9ST, Fife, Scotland
[2] Univ St Andrews, Ctr Biomol Sci, St Andrews KY16 9ST, Fife, Scotland
关键词
D O I
10.1039/b506010a
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Diastereoisomers of bis(amino acid amides) of 2,3-difluorosuccinic acid have been prepared and the erythro- and threoisomers display very different conformations.
引用
收藏
页码:4324 / 4326
页数:3
相关论文
共 28 条
[1]  
ABRAHAMS RJ, 1974, INTERNAL ROTATIONS M
[2]   CONFORMATION IN 2,3-DIFLUOROBUTANES [J].
ANGELINI, G ;
GAVUZZO, E ;
SEGRE, AL ;
SPERANZA, M .
JOURNAL OF PHYSICAL CHEMISTRY, 1990, 94 (25) :8762-8766
[3]   THE REACTIONS OF OZONE WITH ORGANIC COMPOUNDS [J].
BAILEY, PS .
CHEMICAL REVIEWS, 1958, 58 (05) :925-1010
[4]   The preferred conformation of α-fluoroamides [J].
Banks, JW ;
Batsanov, AS ;
Howard, JAK ;
O'Hagan, D ;
Rzepa, HS ;
Martin-Santamaria, S .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1999, (11) :2409-2411
[5]   ORGANIC REACTIONS OF FLUOROXY-COMPOUNDS - STEREOCHEMISTRY OF ADDITION OF FLUOROXYTRIFLUOROMETHANE TO STILBENES [J].
BARTON, DHR ;
HESSE, RH ;
JACKMAN, GP ;
OGUNKOYA, L ;
PECHET, MM .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1974, (07) :739-742
[6]   The C-F bond as a tool in the conformational control of amides [J].
Briggs, CRS ;
O'Hagan, D ;
Howard, JAK ;
Yufit, DS .
JOURNAL OF FLUORINE CHEMISTRY, 2003, 119 (01) :9-13
[7]   The observation of a large gauche preference when 2-fluoroethylamine and 2-fluoroethanol become protonated [J].
Briggs, CRS ;
Allen, MJ ;
O'Hagan, D ;
Tozer, DJ ;
Slawin, AMZ ;
Goeta, AE ;
Howard, JAK .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2004, 2 (05) :732-740
[8]   Solid state and theoretical evaluation of β-fluoroethyl esters indicate a fluorine-ester gauche effect [J].
Briggs, CRS ;
O'Hagan, D ;
Rzepa, HS ;
Slawin, AMZ .
JOURNAL OF FLUORINE CHEMISTRY, 2004, 125 (01) :19-25
[9]   TREATMENT OF DIMETHYL (+)-L-TARTRATE WITH SULFUR-TETRAFLUORIDE [J].
BURMAKOV, AI ;
MOTNYAK, LA ;
KUNSHENKO, BV ;
ALEXEEVA, LA ;
YAGUPOLSKII, LM .
JOURNAL OF FLUORINE CHEMISTRY, 1981, 19 (02) :151-161
[10]   Contribution to the study of the Gauche effect. The complete structure of the anti rotamer of 1,2-difluoroethane [J].
Craig, NC ;
Chen, A ;
Suh, KH ;
Klee, S ;
Mellau, GC ;
Winnewisser, BP ;
Winnewisser, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (20) :4789-4790