Rapid acidolysis of benzyl group as a suitable approach for syntheses of peptides naturally produced by oxidative stress and containing 3-nitrotyrosine

Result code in IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61388963%3A_____%2F16%3A00459208" target="_blank" >RIV/61388963:_____/16:00459208 - isvavai.cz</a>

Alternative codes found

RIV/60461373:22330/16:43901710

Result on the web

<a href="http://dx.doi.org/10.1007/s00726-015-2163-2" target="_blank" >http://dx.doi.org/10.1007/s00726-015-2163-2</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1007/s00726-015-2163-2" target="_blank" >10.1007/s00726-015-2163-2</a>

Result language

angličtina

Original language name

Rapid acidolysis of benzyl group as a suitable approach for syntheses of peptides naturally produced by oxidative stress and containing 3-nitrotyrosine

Original language description

3-Nitrotyrosine (Nit) belongs to products of oxidative stress and could probably influence conformation of neurodegenerative proteins. Syntheses of peptides require availability of suitable synthon for introduction of Nit residue. Common phenolic protection groups are more acid labile, when they are attached to Nit residue. We have found that Fmoc-Nit(Bn)-OH is a good building block for syntheses of Nit containing peptides by Fmoc/tBu strategy. Interestingly, the peptides containing multiple Nit residues can be available solely by use of Fmoc-Nit(Bn)-OH synthon. Bn is removed rapidly with ca 80 % trifluoroacetic acid in dark. The cleavage of Bn from Fmoc-Nit(Bn)-OH proceeds via pseudo-first order mechanism with activation barrier 32 kcal mol(-1) and rate k = 15.3 s(-1) at 20 A degrees C. This rate is more than 2,000,000 times faster than that for cleavage of benzyl from Tyr(Bn).

Czech name

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Czech description

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Type

J_x - Unclassified - Peer-reviewed scientific article (Jimp, Jsc and Jost)

CEP classification

CE - Biochemistry

OECD FORD branch

—

Project

<a href="/en/project/GA14-00431S" target="_blank" >GA14-00431S: 3-Nitro-L-tyrosine in structures of neurodegenerative proteins</a><br>

Continuities

I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Publication year

2016

Confidentiality

S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Name of the periodical

Amino Acids

ISSN

0939-4451

e-ISSN

—

Volume of the periodical

48

Issue of the periodical within the volume

4

Country of publishing house

AT - AUSTRIA

Number of pages

12

Pages from-to

1087-1098

UT code for WoS article

000372551100018

EID of the result in the Scopus database

2-s2.0-84954319068