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  Analogs of phalloidin D‐Abu†‐Lys7‐phalloin, an F‐actin binding analog, its rhodamine conjugate (RLP) a novel fluorescent F‐actin‐probe, and D‐Ala‡‐Leu7‐phalloin, an inert peptide

Wieland, T., Miura, T., & Seeliger, A. (1983). Analogs of phalloidin D‐Abu†‐Lys7‐phalloin, an F‐actin binding analog, its rhodamine conjugate (RLP) a novel fluorescent F‐actin‐probe, and D‐Ala‡‐Leu7‐phalloin, an inert peptide. International journal of peptide and protein research, 22(1), 3-10. doi:10.1111/j.1399-3011.1983.tb03071.x.

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Item Permalink: http://hdl.handle.net/21.11116/0000-0003-720C-0 Version Permalink: http://hdl.handle.net/21.11116/0000-0003-720D-F
Genre: Journal Article

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IntJPeptProtRes_21_1983_3.pdf (Any fulltext), 505KB
 
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 Creators:
Wieland, Theodor1, Author              
Miura, Tamiko, Author
Seeliger, Annemarie1, Author              
Affiliations:
1Max Planck Institute for Medical Research, Max Planck Society, ou_1125545              

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Free keywords: peptide cyclization; Savige‐Fontana reaction; tryptathionine
 Abstract: The analogs [D‐Abu2‐Lys7]‐phalloin (1) and [D‐Ala2‐Leu7]‐phalloin (2) are obtained by cyclization of the monocyclic thioether peptides 5 and 7 with DCCI and diphenylphosphoro‐azidate respectively. For the synthesis of 5 and 7 an intramolecular Savige‐Fontana reaction of the linear heptapeptide tert.‐butylesters 4 and 6 is applied. On treatment in dilute solution with TFA the classically synthesized peptides 4 and 6 lose their N‐terminal Boc groups thus giving rise to the reaction of the Hpi residues with the released cysteine SH‐groups. The lysine analog 1 binds to F‐actin with an association constant of 1.3 times 10‐6M whereas analog 2 exhibits practically no affinity. By reaction of 1 with tetramethyl‐rhodaminyl‐isothiocyanate a fluorescent derivative, rhoda‐minyl‐lysine‐phallotoxin (RLP), is obtained as a novel fluorescent probe for the visualization of F‐actin in cell preparations.

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Language(s): eng - English
 Dates: 1982-03-081982-05-102009-01-121983-01
 Publication Status: Published in print
 Pages: 8
 Publishing info: -
 Table of Contents: -
 Rev. Type: Peer
 Degree: -

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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: 22 (1) Sequence Number: - Start / End Page: 3 - 10 Identifier: ISSN: 0367-8377
ISSN: 0300-9769