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.

Basic information

Original name

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

Authors

THARRA, Prabhakara Rao (356 India, belonging to the institution), Andrey MIKHAYLOV (643 Russian Federation, belonging to the institution), Jiří ŠVEJKAR (203 Czech Republic, belonging to the institution), Marina GYSIN, Sven N. HOBBIE and Jakub ŠVENDA (203 Czech Republic, guarantor, belonging to the institution)

Edition

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

Other information

Language

English

Type of outcome

Článek v odborném periodiku

Field of Study

10400 1.4 Chemical sciences

Country of publisher

Germany

Confidentiality degree

není předmětem státního či obchodního tajemství

References:

URL

Impact factor

Impact factor: 16.600

RIV identification code

RIV/00216224:14310/22:00125752

Organization unit

Faculty of Science

DOI

http://dx.doi.org/10.1002/anie.202116520

UT WoS

000762126500001

Keywords in English

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

Abstract

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.

Links

EF16_025/0007381, research and development project

Name: Preklinická progrese nových organických sloučenin s cílenou biologickou aktivitou

EF16_027/0008360, research and development project

Name: Postdoc@MUNI

GA20-11898S, research and development project

Name: Syntéza a biologické testování analogů přírodních antibiotik bactobolinů

Investor: Czech Science Foundation

LM2018127, research and development project

Name: Česká infrastruktura pro integrativní strukturní biologii (Acronym: CIISB)

Investor: Ministry of Education, Youth and Sports of the CR

LM2018130, research and development project

Name: Národní infrastruktura chemické biologie (Acronym: CZ-OPENSCREEN)

Investor: Ministry of Education, Youth and Sports of the CR

Citovat

THARRA, Prabhakara Rao, Andrey MIKHAYLOV, Jiří ŠVEJKAR, Marina GYSIN, Sven N. HOBBIE and Jakub ŠVENDA. Short Synthesis of (+)-Actinobolin: Simple Entry to Complex Small-Molecule Inhibitors of Protein Synthesis. Angewandte Chemie International Edition. Wiley VCHGmbH, 2022, vol. 61, No 17, p. 1-6. ISSN 1433-7851. Available from: https://dx.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 = {http://dx.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 and Jakub ŠVENDA. Short Synthesis of (+)-Actinobolin: Simple Entry to Complex Small-Molecule Inhibitors of Protein Synthesis. \textit{Angewandte Chemie International Edition}. Wiley VCHGmbH, 2022, vol.~61, No~17, p.~1-6. ISSN~1433-7851. Available from: https://dx.doi.org/10.1002/anie.202116520.

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