Short Synthesis of (+)-Actinobolin: Simple Entry to Complex
Small-Molecule Inhibitors of Protein Synthesis

J 2022

Short Synthesis of (+)-Actinobolin: Simple Entry to Complex Small-Molecule Inhibitors of Protein Synthesis

THARRA, Prabhakara Rao; Andrey MIKHAYLOV; Jiří ŠVEJKAR; Marina GYSIN; Sven N. HOBBIE et. al.

Základní údaje

Originální název

Short Synthesis of (+)-Actinobolin: Simple Entry to Complex Small-Molecule Inhibitors of Protein Synthesis

Autoři

THARRA, Prabhakara Rao; Andrey MIKHAYLOV; Jiří ŠVEJKAR; Marina GYSIN; Sven N. HOBBIE a Jakub ŠVENDA

Vydání

Angewandte Chemie International Edition, Wiley VCHGmbH, 2022, 1433-7851

Další údaje

Jazyk

angličtina

Typ výsledku

Článek v odborném periodiku

Obor

10400 1.4 Chemical sciences

Stát vydavatele

Německo

Utajení

není předmětem státního či obchodního tajemství

Odkazy

URL

Impakt faktor

Impact factor: 16.600

Kód RIV

RIV/00216224:14310/22:00125752

Organizační jednotka

Přírodovědecká fakulta

DOI

https://doi.org/10.1002/anie.202116520

UT WoS

000762126500001

EID Scopus

2-s2.0-85125393898

Klíčová slova anglicky

Antibiotics; Natural Products; Organic Synthesis; Radical Chemistry; Ribosome Inhibitors

Štítky

14313010, CF SAXS, rivok

Příznaky

Mezinárodní význam, Recenzováno

Změněno: 7. 5. 2025 10:52, Mgr. Marie Novosadová Šípková, DiS.

Anotace

V originále

We report a concise synthesis of the naturally occurring protein synthesis inhibitor (+)-actinobolin (1). The densely functionalized and stereochemically complex molecular structure of 1 was assembled from (-)-quinic acid, L-threonine, and L-alanine as the principal components. Our route is based around a convergent strategy that features conjugate addition of an alpha-amino radical in the key fragment-coupling step. The dramatically simplified synthesis of (+)-actinobolin proceeding in 9 steps with 18 % overall yield has practical implications for analog preparation, as demonstrated herein.

Návaznosti

EF16_025/0007381, projekt VaV

Název: Preklinická progrese nových organických sloučenin s cílenou biologickou aktivitou

EF16_027/0008360, projekt VaV

Název: Postdoc@MUNI

GA20-11898S, projekt VaV

Název: Syntéza a biologické testování analogů přírodních antibiotik bactobolinů

Investor: Grantová agentura ČR, Syntéza a biologické testování analogů přírodních antibiotik bactobolinů

90127, velká výzkumná infrastruktura

Název: CIISB II

90130, velká výzkumná infrastruktura

Název: CZ-OPENSCREEN III

Citovat

THARRA, Prabhakara Rao; Andrey MIKHAYLOV; Jiří ŠVEJKAR; Marina GYSIN; Sven N. HOBBIE a Jakub ŠVENDA. Short Synthesis of (+)-Actinobolin: Simple Entry to Complex Small-Molecule Inhibitors of Protein Synthesis. Angewandte Chemie International Edition. Wiley VCHGmbH, 2022, roč. 61, č. 17, s. 1-6. ISSN 1433-7851. Dostupné z: https://doi.org/10.1002/anie.202116520.

@article{1850761,
   author = {Tharra, Prabhakara Rao and Mikhaylov, Andrey and Švejkar, Jiří and Gysin, Marina and Hobbie, Sven N. and Švenda, Jakub},
   article_number = {17},
   doi = {https://doi.org/10.1002/anie.202116520},
   keywords = {Antibiotics; Natural Products; Organic Synthesis; Radical Chemistry; Ribosome Inhibitors},
   language = {eng},
   issn = {1433-7851},
   journal = {Angewandte Chemie International Edition},
   title = {Short Synthesis of (+)-Actinobolin: Simple Entry to Complex Small-Molecule Inhibitors of Protein Synthesis},
   url = {https://onlinelibrary.wiley.com/doi/full/10.1002/anie.202116520},
   volume = {61},
   year = {2022}
}

TY  - JOUR
ID  - 1850761
AU  - Tharra, Prabhakara Rao - Mikhaylov, Andrey - Švejkar, Jiří - Gysin, Marina - Hobbie, Sven N. - Švenda, Jakub
PY  - 2022
TI  - Short Synthesis of (+)-Actinobolin: Simple Entry to Complex Small-Molecule Inhibitors of Protein Synthesis
JF  - Angewandte Chemie International Edition
VL  - 61
IS  - 17
SP  - 1-6
EP  - 1-6
PB  - Wiley VCHGmbH
SN  - 14337851
KW  - Antibiotics
KW  - Natural Products
KW  - Organic Synthesis
KW  - Radical Chemistry
KW  - Ribosome Inhibitors
UR  - https://onlinelibrary.wiley.com/doi/full/10.1002/anie.202116520
N2  - We report a concise synthesis of the naturally occurring protein synthesis inhibitor (+)-actinobolin (1). The densely functionalized and stereochemically complex molecular structure of 1 was assembled from (-)-quinic acid, L-threonine, and L-alanine as the principal components. Our route is based around a convergent strategy that features conjugate addition of an alpha-amino radical in the key fragment-coupling step. The dramatically simplified synthesis of (+)-actinobolin proceeding in 9 steps with 18 % overall yield has practical implications for analog preparation, as demonstrated herein.
ER  -

THARRA, Prabhakara Rao; Andrey MIKHAYLOV; Jiří ŠVEJKAR; Marina GYSIN; Sven N. HOBBIE a Jakub ŠVENDA. Short Synthesis of (+)-Actinobolin: Simple Entry to Complex Small-Molecule Inhibitors of Protein Synthesis. \textit{Angewandte Chemie International Edition}. Wiley VCHGmbH, 2022, roč.~61, č.~17, s.~1-6. ISSN~1433-7851. Dostupné z: https://doi.org/10.1002/anie.202116520.

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