SYNTHESIS AND STEREOCHEMISTRY OF OPTICALLY-ACTIVE BILIVERDIN CYCLIC ESTERS

被引:12
作者
BOIADJIEV, SE [1 ]
ANSTINE, DT [1 ]
LIGHTNER, DA [1 ]
机构
[1] UNIV NEVADA,DEPT CHEM,RENO,NV 89557
关键词
D O I
10.1016/0957-4166(95)00098-A
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
(beta S,beta'S)-Dimethylmesobiliverdin-XIII alpha dimethyl ester exhibits a positive long wavelength circular dichroism Cotton effect (Delta epsilon(644)(max)=+6.1) in CHCl3, indicating an excess of the P-helical conformation of the pigment. But when the pigment's propionic acids are linked together by -(CH2)(n)- chains in cyclic esters, the choice of cyclic ester conformation and pigment helicity is governed by the number (n) of CH2 units, with Delta epsilon near 640 nm varying from positive when n=1, 5 and 6, to negative when n=2, 3 and 4.
引用
收藏
页码:901 / 912
页数:12
相关论文
共 20 条
  • [1] ABSOLUTE-CONFIGURATION OF BILIRUBIN CONFORMATIONAL ENANTIOMERS
    BOIADJIEV, SE
    PERSON, RV
    PUZICHA, G
    KNOBLER, C
    MAVERICK, E
    TRUEBLOOD, KN
    LIGHTNER, DA
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (26) : 10123 - 10133
  • [2] ABSTRACTS ON THE CHEMISTRY OF PYRROLE PIGMENTS .37. BRIDGED BILE-PIGMENTS - N21-N24-METHYLENE ETIOBILIVERDIN-IV-GAMMA AND N21-N24-METHYLENE AETIOBILIRUBIN-IV-GAMMA
    FALK, H
    THIRRING, K
    [J]. TETRAHEDRON, 1981, 37 (04) : 761 - 766
  • [3] Falk H., 1989, CHEM LINEAR OLIGOPYR
  • [4] Composition of biliverdins (uteroverdins) and bilirubins
    Fischer, H
    Plieninger, H
    [J]. NATURWISSENSCHAFTEN, 1942, 30 : 382 - 387
  • [5] FISCHER H, 1942, Z PHYSIOL CHEM, V274, P231
  • [6] GOSSAUER A, 1994, CHIMIA, V48, P352
  • [7] MOLECULAR-STRUCTURE OF THE BILIN BINDING-PROTEIN (BBP) FROM PIERIS-BRASSICAE AFTER REFINEMENT AT 2.0-A RESOLUTION
    HUBER, R
    SCHNEIDER, M
    MAYR, I
    MULLER, R
    DEUTZMANN, R
    SUTER, F
    ZUBER, H
    FALK, H
    KAYSER, H
    [J]. JOURNAL OF MOLECULAR BIOLOGY, 1987, 198 (03) : 499 - 513
  • [8] HELICALLY FIXED CHIRAL BILIRUBINS AND BILIVERDINS - A NEW INSIGHT INTO THE CONFORMATIONAL, ASSOCIATIVE AND DYNAMIC FEATURES OF LINEAR TETRAPYRROLS
    KROIS, D
    LEHNER, H
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1993, (07): : 1351 - 1360
  • [9] HELICALLY SHAPED BILIRUBINS - NATURAL OPTICAL-ACTIVITY AND CHEMICAL CORRELATION OF M AND P BACKBONE HELICITY WITH BILIVERDINS
    KROIS, D
    LEHNER, H
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1993, (10): : 1837 - 1840
  • [10] CONFORMATION CONTROL OF BILATRIENES BY PEPTIDES - A SURVEY
    KROIS, D
    LEHNER, H
    [J]. MONATSHEFTE FUR CHEMIE, 1991, 122 (1-2): : 89 - 100