Enantioselection in bilirubin analogs with only one propionic acid group

被引:8
作者
Boiadjiev, SE [1 ]
Lightner, DA [1 ]
机构
[1] UNIV NEVADA, DEPT CHEM, RENO, NV 89557 USA
基金
美国国家卫生研究院;
关键词
D O I
10.1016/S0957-4166(97)00481-3
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Enantiopure synthetic bilirubin analogs (1 and 2) with only a single beta-methyl propionic acid group adopt a folded, ridge-tile conformation stabilized by intramolecular hydrogen bonding. The beta-methyl group forces the pigment to adopt a left-handed (M) helical conformation, as evidenced by exciton circular dichroism spectra and indicating that one propionic acid group is sufficient to control the pigment's conformation. (C) 1997 Elsevier Science Ltd.
引用
收藏
页码:3603 / 3615
页数:13
相关论文
共 33 条
[1]   BILE PIGMENT STRUCTURES .2. CRYSTAL-STRUCTURE OF MESOBILIRUBIN-IX-ALPHA-BIS(CHLOROFORM) [J].
BECKER, W ;
SHELDRICK, WS .
ACTA CRYSTALLOGRAPHICA SECTION B-STRUCTURAL SCIENCE, 1978, 34 (APR) :1298-1304
[2]   COMPARISON OF BILIARY-EXCRETION OF 4 ISOMERS OF BILIRUBIN-9 IN WISTAR AND HOMOZYGOUS GUNN RATS [J].
BLANCKAERT, N ;
HEIRWEGH, KPM ;
ZAMAN, Z .
BIOCHEMICAL JOURNAL, 1977, 164 (01) :229-236
[3]   ABSOLUTE-CONFIGURATION OF BILIRUBIN CONFORMATIONAL ENANTIOMERS [J].
BOIADJIEV, SE ;
PERSON, RV ;
PUZICHA, G ;
KNOBLER, C ;
MAVERICK, E ;
TRUEBLOOD, KN ;
LIGHTNER, DA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (26) :10123-10133
[4]   HYDROGEN-BONDING AND PI-STACKING IN DIPYRRINONE ACID DIMERS OF XANTHOBILIRUBIC ACID AND CHIRAL ANALOGS [J].
BOIADJIEV, SE ;
ANSTINE, DT ;
MAVERICK, E ;
LIGHTNER, DA .
TETRAHEDRON-ASYMMETRY, 1995, 6 (09) :2253-2270
[5]   INTERMOLECULAR HYDROGEN-BONDING IN PI-FACIAL DIPYRRINONE DIMERS AS MOLECULAR CAPSULES [J].
BOIADJIEV, SE ;
ANSTINE, DT ;
LIGHTNER, DA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (34) :8727-8736
[6]   CONFORMATIONAL-ANALYSIS OF AN OPTICALLY-ACTIVE BILIRUBIN DIMETHYL ESTER AND BIS-N,N-DIMETHYL AMIDE BY CIRCULAR-DICHROISM, NMR AND MOLECULAR-DYNAMICS [J].
BOIADJIEV, SE ;
ANSTINE, DT ;
LIGHTNER, DA .
TETRAHEDRON-ASYMMETRY, 1994, 5 (10) :1945-1964
[7]   STRUCTURE OF BILIRUBIN [J].
BONNETT, R ;
DAVIES, JE ;
HURSTHOUSE, MB ;
SHELDRICK, GM .
PROCEEDINGS OF THE ROYAL SOCIETY SERIES B-BIOLOGICAL SCIENCES, 1978, 202 (1147) :249-268
[8]  
BOYER PD, 1994, SEMINARS LIVER DIS, V269, P323
[9]  
Falk H., 1989, The Chemistry of Linear Oligopyrroles and Bile Pigments
[10]  
Harada N., 1983, CIRCULAR DICHROIC SP