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  ANALOGS OF AMANIN Synthesis of Ile3‐Amaninamide and its Diastereoisomeric (S)‐Sulfoxide

Zanotti, G., Birr, C., & Wieland, T. (1981). ANALOGS OF AMANIN Synthesis of Ile3‐Amaninamide and its Diastereoisomeric (S)‐Sulfoxide. International journal of peptide and protein research, 18(2), 162-168. doi:10.1111/j.1399-3011.1981.tb02054.x.

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Genre: Journal Article
Alternative Title : Analogs of amanin. Synthesis of Ile3-amaninamide and its diastereoisomeric (S)-sulfoxide

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IntJPeptProtRes_18_1981_162.pdf (Any fulltext), 461KB
 
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 Creators:
Zanotti, Giancarlo1, Author              
Birr, Christian1, Author              
Wieland, Theodor1, Author              
Affiliations:
1Max Planck Institute for Medical Research, Max Planck Society, ou_1125545              

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Free keywords: amatoxin; bicyclic peptides; inhibition of eukaryotic RNA polymerase; tryptathionine
 Abstract: Ile3-amaninamide (3-R) and its diastereomeric sulfoxide (3-S) are obtained by oxidation of the bicyclic thioether peptide 2 by hydrogen peroxide in acetic acid. 2 was prepared by an intramolecular Savige-Fontana reaction of the linear octapeptide tert.-butylester 4 whose N-terminal Boc-Hpi residue on treatment with TFA loses the Boc group and reacts under thioether formation with the released cysteine-SH. The concomitantly deprotected carboxyl terminus is coupled intramolecularly with the free amino group of the secocompound 5 using the MA or DCCI method, thus forming the homodetic peptide ring. Compounds 3-R and 3-S agree very well with analog samples in chiroptical behavior. Thioether 2 and sulfoxide 3-R exert 50% inhibition of RNA polymerase II (or B) from Drosophila melanogaster in 10(-6) M solution whereas Ki of 3-S is about five times higher.

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Language(s): eng - English
 Dates: 1981-02-051981-02-252009-01-121981-08
 Publication Status: Published in print
 Pages: 7
 Publishing info: -
 Table of Contents: -
 Rev. Type: Peer
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Title: International journal of peptide and protein research
Source Genre: Journal
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Publ. Info: Copenhagen : Munksgaard
Pages: - Volume / Issue: 18 (2) Sequence Number: - Start / End Page: 162 - 168 Identifier: ISSN: 0367-8377
ISSN: 0300-9769