Turn formation initiated by a bissulfoximine motif: Synthesis and structural investigation

被引:43
作者
Bolm, C [1 ]
Muller, D [1 ]
Hackenberger, PR [1 ]
机构
[1] Rhein Westfal TH Aachen, Inst Organ Chem, D-52056 Aachen, Germany
关键词
D O I
10.1021/ol017188r
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHICS] Bissulfoximines containing heterochiral SulfCO-SulfCO units may be used as molecular templates, which induce U-shaped conformations in peptidelike structures. The synthesis of such molecules has been investigated, and the structural requirements of this new turn motif have been identified.
引用
收藏
页码:893 / 896
页数:4
相关论文
共 38 条
[1]  
Ball J B, 1990, J Mol Recognit, V3, P55, DOI 10.1002/jmr.300030202
[2]  
Belvisi L, 1999, EUR J ORG CHEM, V1999, P389
[3]  
Belvisi L, 2000, EUR J ORG CHEM, V2000, P695, DOI 10.1002/(SICI)1099-0690(200003)2000:5<695::AID-EJOC695>3.0.CO
[4]  
2-V
[5]   Ring-closing metathesis of olefinic peptides: Design, synthesis, and structural characterization of macrocyclic helical peptides [J].
Blackwell, HE ;
Sadowsky, JD ;
Howard, RJ ;
Sampson, JN ;
Chao, JA ;
Steinmetz, WE ;
O'Leary, DJ ;
Grubbs, RH .
JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (16) :5291-5302
[6]  
Bolm C, 2001, CHEM-EUR J, V7, P1118, DOI 10.1002/1521-3765(20010302)7:5<1118::AID-CHEM1118>3.0.CO
[7]  
2-3
[8]   Sulfoximines in pseudopeptides [J].
Bolm, C ;
Kahmann, JD ;
Moll, G .
TETRAHEDRON LETTERS, 1997, 38 (07) :1169-1172
[9]   An efficient resolution of (+/-)-S-methyl-S-phenylsulfoximine with (+)-10-camphorsulfonic acid by the method of half-quantities [J].
Brandt, J ;
Gais, HJ .
TETRAHEDRON-ASYMMETRY, 1997, 8 (06) :909-912
[10]   Stereochemical control of hairpin formation in β-peptides containing dinipecotic acid reverse turn segments [J].
Chung, YJ ;
Huck, BR ;
Christianson, LA ;
Stanger, HE ;
Krauthäuser, S ;
Powell, DR ;
Gellman, SH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (17) :3995-4004