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  Analogs of viroidin. Synthesis of four virotoxin‐like F‐actin binding heptapeptides with one less hydroxyl group in the dihydroxy‐proline ring

Kahl, J.-U., Vlasov, G. P., Seeliger, A., & Wieland, T. (1984). Analogs of viroidin. Synthesis of four virotoxin‐like F‐actin binding heptapeptides with one less hydroxyl group in the dihydroxy‐proline ring. International Journal of Peptide and Protein Research, 23(5), 543-550. doi:10.1111/j.1399-3011.1984.tb02756.x.

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Item Permalink: http://hdl.handle.net/21.11116/0000-0006-8E92-5 Version Permalink: http://hdl.handle.net/21.11116/0000-0006-8E93-4
Genre: Journal Article

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IntJPeptProtRes_23_1984_543.pdf (Any fulltext), 495KB
 
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 Creators:
Kahl, Jens-Uwe1, Author              
Vlasov , Genadi P., Author
Seeliger, Annemarie1, Author              
Wieland, Theodor1, Author              
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1Max Planck Institute for Medical Research, Max Planck Society, ou_1125545              

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Free keywords: F‐actin binding,methylsulfonyltryptophan, methylthiotryptophan, phallotoxins,toxic fungal peptides
 Abstract: The vitroxins, toxic cyclic heptapeptides from Amanita virosa fungi, contain a 3,4-dihydroxy-L-proline, an imino acid scarcely accessible in greater amounts. Therefore in the syntheses of the analogs described this imino acid was replaced by 4-cis-hydroxy-L-proline, a component of the analogously toxic phallotoxins. The following syntheses are described: 1a = cyclo (L-alanyl-D-threonyl-D-seryl-L-4-cis-hydroxy-L-prolyl-L-alanyl-2- methylthio-L-tryptophyl-L-leucyl), 1b = 1a but with 2-methylsulfonyl-L-tryptophan in position 6, 2a = cyclic (L-valyl-D-threonyl-D-seryl-4-cis-hydroxy-L-prolyl-L-alanyl-2- methylthio-L-tryptophyl-hydroxyl-L-leucyl), and 2b = 2a, but with 2-methylsulfonyl-L-tryptophan in position 6. In a test for binding strength to rabbit muscle F-actin 2b and 2a exhibited about 40% of that of demethylphalloin. Analogs 1a and 2b have not been tested.

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Language(s): eng - English
 Dates: 1983-08-251983-09-301984-05
 Publication Status: Published in print
 Pages: 8
 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: Denmark : Copenhagen, Munksgaard
Pages: - Volume / Issue: 23 (5) Sequence Number: - Start / End Page: 543 - 550 Identifier: ISSN: 0367-8377