1ST EXAMPLE OF DIASTEREOTOPIC FACE ACTIVATION AND CHIRAL RECOGNITION WITHOUT METAL ASSISTANCE - A NOVEL 5-DEAZAFLAVIN ENZYME MODEL

被引：14

作者：

KAWAMOTO, T

TOMISHIMA, M

KUNITOMO, J

YONEDA, F

HAYAMI, J

机构：

[1] KYOTO UNIV,FAC PHARMACEUT SCI,SAKYO KU,KYOTO 60601,JAPAN

[2] KYOTO UNIV,GRAD SCH HUMAN & ENVIRONM STUDIES,SAKYO KU,KYOTO 60601,JAPAN

来源：

TETRAHEDRON LETTERS | 1992年 / 33卷 / 47期

关键词：

D O I：

10.1016/S0040-4039(00)60865-1

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A chiral 5-deazaflavin 1 with 2-hydroxynaphthyl group at N(3) position of the pyrimidine ring moiety was synthesized. 1 underwent, in the absence of magnesium ion, a ''(net) hydride transfer'' from BNAH to C(5) almost exclusively on the face where OH group is present. It was also the case with PNPH, and enantioselectivity for PNPH by 1 was higher in the absence of magnesium ion than in its presence. These results indicate that the ''diastereotopic face activation'' in 1 is operated as well as chiral recognition for PNPH by 1.

引用

页码：7173 / 7176

页数：4

共 17 条

[1] PROPOSED STRUCTURE FOR COENZYME-F-420 FROM METHANOBACTERIUM
EIRICH, LD
VOGELS, GD
WOLFE, RS
[J]. BIOCHEMISTRY, 1978, 17 (22) : 4583 - 4593
[2] FACTOR-390 CHROMOPHORES - PHOSPHODIESTER BETWEEN AMP OR GMP AND METHANOGEN FACTOR-420
HAUSINGER, RP
ORMEJOHNSON, WH
WALSH, C
[J]. BIOCHEMISTRY, 1985, 24 (07) : 1629 - 1633
[3] DIASTEREOFACE-DIFFERENTIATING REACTIONS IN A NEW TYPE OF ENZYME BOUND 5-DEAZAFLAVIN MODEL
KAWAMOTO, T
TANAKA, K
KURODA, Y
YONEDA, F
[J]. CHEMISTRY LETTERS, 1990, (07) : 1197 - 1200
[4] SYNTHESIS AND REACTION OF A NEW TYPE OF 5-DEAZAFLAVIN WITH AXIAL AND PLANAR CHIRALITY
KAWAMOTO, T
TANAKA, K
YONEDA, F
HAYAMI, J
[J]. TETRAHEDRON LETTERS, 1989, 30 (52) : 7431 - 7434
[5] SYNTHESIS AND REACTION OF NOVEL 5-DEAZAFLAVINS WITH AXIAL CHIRALITY AT PYRIMIDINE RING MOIETY
KAWAMOTO, T
TOMISHIMA, M
YONEDA, F
HAYAMI, J
[J]. TETRAHEDRON LETTERS, 1992, 33 (22) : 3169 - 3172
[6] DIASTEREOFACE DIFFERENTIATING (NET) HYDRIDE TRANSFER IN NOVEL 5-DEAZAFLAVINS MODIFIED AT PYRIMIDINE RING
KAWAMOTO, T
TOMISHIMA, M
YONEDA, F
HAYAMI, J
[J]. TETRAHEDRON LETTERS, 1992, 33 (22) : 3173 - 3176
[7] OHNISHI Y, 1975, Tetrahedron Letters, V44, P3813
[8] REDUCTION BY A MODEL OF NAD(P)H .14. MECHANISTIC CONSIDERATION ON ROLE OF METAL-ION
OHNO, A
KIMURA, T
YAMAMOTO, H
KIM, SG
OKA, S
OHNISHI, Y
[J]. BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1977, 50 (06) : 1535 - 1538
[9] OHNO A, 1979, J AM CHEM SOC, V101, P7036, DOI 10.1021/ja00517a043
[10] COENZYME MODELS .48. NOVEL DIASTEREO-DIFFERENTIATING HYDROGEN TRANSFER AND ROPE-SKIPPING RACEMIZATION IN CHIRAL FLAVINOPHANES AND 5-DEAZAFLAVINOPHANES
SHINKAI, S
YAMAGUCHI, T
KAWASE, A
MANABE, O
KELLOGG, RM
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (13) : 4935 - 4940

← 1 2 →