Thiazole–amino acids: influence of thiazole ring on conformational properties of amino acid residues
The result's identifiers
Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61388963%3A_____%2F21%3A00542031" target="_blank" >RIV/61388963:_____/21:00542031 - isvavai.cz</a>
Result on the web
<a href="https://doi.org/10.1007/s00726-021-02974-0" target="_blank" >https://doi.org/10.1007/s00726-021-02974-0</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1007/s00726-021-02974-0" target="_blank" >10.1007/s00726-021-02974-0</a>
Alternative languages
Result language
angličtina
Original language name
Thiazole–amino acids: influence of thiazole ring on conformational properties of amino acid residues
Original language description
Post-translational modified thiazole–amino acid (Xaa–Tzl) residues have been found in macrocyclic peptides (e.g., thiopeptides and cyanobactins), which mostly inhibit protein synthesis in Gram + bacteria. Conformational study of the series of model compounds containing this structural motif with alanine, dehydroalanine, dehydrobutyrine and dehydrophenylalanine were performed using DFT method in various environments. The solid-state crystal structure conformations of thiazole–amino acid residues retrieved from the Cambridge Structural Database were also analysed. The studied structural units tend to adopt the unique semi-extended β2 conformation, which is stabilised mainly by N–H⋯NTzl hydrogen bond, and for dehydroamino acids also by π-electron conjugation. The conformational preferences of amino acids with a thiazole ring were compared with oxazole analogues and the role of the sulfur atom in stabilising the conformations of studied peptides was discussed.
Czech name
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Czech description
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Classification
Type
J<sub>imp</sub> - Article in a specialist periodical, which is included in the Web of Science database
CEP classification
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OECD FORD branch
10403 - Physical chemistry
Result continuities
Project
—
Continuities
I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace
Others
Publication year
2021
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů
Data specific for result type
Name of the periodical
Amino Acids
ISSN
0939-4451
e-ISSN
1438-2199
Volume of the periodical
53
Issue of the periodical within the volume
5
Country of publishing house
AT - AUSTRIA
Number of pages
14
Pages from-to
673-686
UT code for WoS article
000638833600001
EID of the result in the Scopus database
2-s2.0-85104241621