当前位置： SCI文献检索 > ARCHIVES OF BIOCHEMISTRY AND BIOPHYSICS期刊下所有文献 > Formation of diastereoisomeric 3a-hydroxypyrroloindoles from a tryptophan residue analog mediated by iron (II)-EDTA and L-ascorbate.

Formation of diastereoisomeric 3a-hydroxypyrroloindoles from a tryptophan residue analog mediated by iron (II)-EDTA and L-ascorbate.

Abstract：

:Oxygenation of a tryptophan residue analog by ascorbate in the presence of catalytic amounts of iron(II) and ethylenediaminetetraacetic acid (EDTA) has been studied. Under physiological conditions, reaction of the tryptophan derivative (N-t-butoxycarbonyl-L-tryptophan) with Fe(II)-EDTA and ascorbate resulted mainly in the oxygenation of the indole moiety of the substrate. In this reaction, cis and trans diastereoisomeric alcohols 3a-hydroxy-1-t-butoxycarbonyl-1,2,3,3a,8,8a-hexahydropyrrolo[2,3- b]indoles have been successfully identified in the metal-catalyzed free radical oxidation of indole compounds. Hydroxylation at C-5 and C-6 and a ring opening reaction between C-2 and C-3 have also been confirmed. The reaction of Fe(II)-EDTA/ascorbate with the tryptophan derivative was apparently nonselective with regard to position and was significantly suppressed by the hydroxyl radical scavengers (mannitol and dimethylsulfoxide), suggesting the participation of the hydroxyl radical as the actual oxidizing species.

journal_name

Arch Biochem Biophys

journal_title

Archives of biochemistry and biophysics

authors

Uchida K,Enomoto N,Itakura K,Kawakishi S

doi

10.1016/0003-9861(90)90456-9

subject

Has Abstract

pub_date

1990-05-15 00:00:00

pages

14-20

issue

1

eissn

0003-9861

issn

1096-0384

pii

0003-9861(90)90456-9

journal_volume

279

pub_type

杂志文章

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