α-Amino Acid-Isosteric α-Amino Tetrazoles

Ting Zhao; Katarzyna Kurpiewska; Justyna Kalinowska-Tłuścik; Eberhardt Herdtweck; Alexander Dömling

doi:10.1002/chem.201504520

α-Amino Acid-Isosteric α-Amino Tetrazoles

Ting Zhao, Katarzyna Kurpiewska, Justyna Kalinowska-Tłuścik, Eberhardt Herdtweck, Alexander Dömling

Onderzoeksoutput › Academic › peer review

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The synthesis of all 20 common natural proteinogenic and 4 otherα-amino acid-isosteric α-amino tetrazoles has been accomplished, whereby the carboxyl group is replaced by the isosteric 5-tetrazolyl group. The short process involves the use of the key Ugi tetrazole reaction followed by deprotection chemistries. The tetrazole group is bioisosteric to the carboxylic acid and is widely used in medicinal chemistry and drug design. Surprisingly, several of the common α-amino acid-isosteric α-amino tetrazoles are unknown up to now. Therefore a rapid synthetic access to this compound class and non-natural derivatives is of high interest to advance the field.

Originele taal-2	English
Pagina's (van-tot)	3009-3018
Aantal pagina's	10
Tijdschrift	Chemistry
Volume	22
Nummer van het tijdschrift	9
DOI's	https://doi.org/10.1002/chem.201504520
Status	Published - feb.-2016

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CCDC 1410966: Experimental Crystal Structure Determination
Zhao, T. (Contributor), Kurpiewska, K. (Contributor), Kalinowska-Tłus̈cik, J. (Contributor), Herdtweck, E. (Contributor) & Dömling, A. (Contributor), University of Groningen, 6-jul.-2015
DOI: 10.5517/ccdc.csd.cc1jc715
Dataset
CCDC 1501410: Experimental Crystal Structure Determination
Zhao, T. (Contributor), Kurpiewska, K. (Contributor), Kalinowska-Tłus̈cik, J. (Contributor), Herdtweck, E. (Contributor) & Dömling, A. (Contributor), University of Groningen, 29-aug.-2016
DOI: 10.5517/ccdc.csd.cc1mdbly
Dataset
CCDC 1410965: Experimental Crystal Structure Determination
Zhao, T. (Contributor), Kurpiewska, K. (Contributor), Kalinowska-Tłus̈cik, J. (Contributor), Herdtweck, E. (Contributor) & Dömling, A. (Contributor), University of Groningen, 6-jul.-2015
DOI: 10.5517/ccdc.csd.cc1jc704
Dataset

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title = "α-Amino Acid-Isosteric α-Amino Tetrazoles",

abstract = "The synthesis of all 20 common natural proteinogenic and 4 otherα-amino acid-isosteric α-amino tetrazoles has been accomplished, whereby the carboxyl group is replaced by the isosteric 5-tetrazolyl group. The short process involves the use of the key Ugi tetrazole reaction followed by deprotection chemistries. The tetrazole group is bioisosteric to the carboxylic acid and is widely used in medicinal chemistry and drug design. Surprisingly, several of the common α-amino acid-isosteric α-amino tetrazoles are unknown up to now. Therefore a rapid synthetic access to this compound class and non-natural derivatives is of high interest to advance the field.",

author = "Ting Zhao and Katarzyna Kurpiewska and Justyna Kalinowska-T{\l}u{\'s}cik and Eberhardt Herdtweck and Alexander D{\"o}mling",

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year = "2016",

month = feb,

doi = "10.1002/chem.201504520",

language = "English",

volume = "22",

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TY - JOUR

T1 - α-Amino Acid-Isosteric α-Amino Tetrazoles

AU - Zhao, Ting

AU - Kurpiewska, Katarzyna

AU - Kalinowska-Tłuścik, Justyna

AU - Herdtweck, Eberhardt

AU - Dömling, Alexander

PY - 2016/2

Y1 - 2016/2

N2 - The synthesis of all 20 common natural proteinogenic and 4 otherα-amino acid-isosteric α-amino tetrazoles has been accomplished, whereby the carboxyl group is replaced by the isosteric 5-tetrazolyl group. The short process involves the use of the key Ugi tetrazole reaction followed by deprotection chemistries. The tetrazole group is bioisosteric to the carboxylic acid and is widely used in medicinal chemistry and drug design. Surprisingly, several of the common α-amino acid-isosteric α-amino tetrazoles are unknown up to now. Therefore a rapid synthetic access to this compound class and non-natural derivatives is of high interest to advance the field.

AB - The synthesis of all 20 common natural proteinogenic and 4 otherα-amino acid-isosteric α-amino tetrazoles has been accomplished, whereby the carboxyl group is replaced by the isosteric 5-tetrazolyl group. The short process involves the use of the key Ugi tetrazole reaction followed by deprotection chemistries. The tetrazole group is bioisosteric to the carboxylic acid and is widely used in medicinal chemistry and drug design. Surprisingly, several of the common α-amino acid-isosteric α-amino tetrazoles are unknown up to now. Therefore a rapid synthetic access to this compound class and non-natural derivatives is of high interest to advance the field.

U2 - 10.1002/chem.201504520

DO - 10.1002/chem.201504520

M3 - Article

C2 - 26817531

SN - 0947-6539

VL - 22

SP - 3009

EP - 3018

JO - Chemistry

JF - Chemistry

IS - 9

ER -

α-Amino Acid-Isosteric α-Amino Tetrazoles

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CCDC 1410966: Experimental Crystal Structure Determination

CCDC 1501410: Experimental Crystal Structure Determination

CCDC 1410965: Experimental Crystal Structure Determination

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