SYNTHESIS OF OXA ANALOGS OF PORPHOBILINOGEN (PBG) AS PROBES FOR MECHANISTIC STUDIES OF PBG DEAMINASE

被引：22

作者：

DANSODANQUAH, RE

SCOTT, AI

BECKER, D

机构：

[1] TEXAS A&M UNIV SYST,DEPT CHEM,CTR BIOL NMR,COLL STN,TX 77843

[2] TECHNION ISRAEL INST TECHNOL,DEPT CHEM,IL-32000 HAIFA,ISRAEL

来源：

TETRAHEDRON | 1993年 / 49卷 / 36期

关键词：

D O I：

10.1016/S0040-4020(01)88038-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Three oxa analogs of porphobilinogen (PBG) 2, 27, and 29 were synthesized from 3-hydroxymethylfuran. The target molecules were prepared by introducing first the beta-acetate sidechain, then constructing propionate side chains on the furan nucleus into which the aminomethyl group was introduced at position 2 via the corresponding aldehyde.

引用

页码：8195 / 8210

页数：16

共 26 条

[1] THE SYNTHESIS OF 3,4-DISUBSTITUTED FURAN PROSTANOIDS
ANSELL, MF
CATON, MPL
NORTH, PC
[J]. TETRAHEDRON LETTERS, 1981, 22 (18) : 1727 - 1728
[2] NEW SYNTHETIC APPROACH TOWARDS ADRIAMYCIN
BARTON, DHR
DAWES, CC
FRANCESCHI, G
FOGLIO, M
LEY, SV
MAGNUS, PD
MITCHELL, WL
TEMPERELLI, A
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1980, (02): : 643 - 647
[3] BIOSYNTHESIS OF THE NATURAL PORPHYRINS - EXPERIMENTS ON THE RING-CLOSURE STEPS AND WITH THE HYDROXY-ANALOGUE OF PORPHOBILINOGEN
BATTERSBY, AR
FOOKES, CJR
MATCHAM, GWJ
MCDONALD, E
GUSTAFSONPOTTER, KE
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1979, (07) : 316 - 319
[4] THE 1, 4 O-]C SILYL MIGRATIONS OF VARIOUS 3-[(TRIALKYLSILYL)-OXYMETHYL]-FURANS AND 3-[(TRIALKYLSILYL)-OXYMETHYL]-THIOPHENES
BURES, EJ
KEAY, BA
[J]. TETRAHEDRON LETTERS, 1987, 28 (48) : 5965 - 5968
[5] THE REGIOSPECIFIC FORMATION AND REACTIONS OF 4-LITHIO-2-(TERT-BUTYL-DIMETHYLSILYL)-3-(HYDROXYMETHYL)FURAN - AN APPROACH TO 3,4-DISUBSTITUTED FURANS
BURES, EJ
KEAY, BA
[J]. TETRAHEDRON LETTERS, 1988, 29 (11) : 1247 - 1250
[6] TOTAL SYNTHESIS OF NATURAL 20(S)-CAMPTOTHECIN
COREY, EJ
CROUSE, DN
ANDERSON, JE
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1975, 40 (14) : 2140 - 2141
[7] A NEW SYNTHESIS OF SUBSTITUTED FURANS
DANHEISER, RL
STONER, EJ
KOYAMA, H
YAMASHITA, DS
KLADE, CA
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (12) : 4407 - 4413
[8] DAVIES GM, 1972, TETRAHEDRON LETT, V33, P3507
[9] PYRROLE CHEMISTRY .27. 2,3,4-TRISUBSTITUTED PYRROLES AND A 2ND SYNTHESIS OF PORPHOBILINOGEN FROM PYRROLE
FABER, K
ANDERSON, HJ
LOADER, CE
DALEY, AS
[J]. CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1984, 62 (06): : 1046 - 1050
[10] GAETANO DA, 1972, Patent No. 3664992

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