α-Amino Acid-Isosteric α-Amino Tetrazoles

Chemistry : a European Journal
Ting ZhaoAlexander Dömling

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.

References

Aug 31, 1977·Journal of the American Chemical Society·M Waki, J Meienhofer
Mar 1, 1992·Medicinal Research Reviews·J V DunciaP B Timmermans
Mar 1, 1967·Journal of Medicinal Chemistry·G F Holland, J N Pereira
Nov 1, 1967·Journal of Medicinal Chemistry·S K Figdor, M S von ittenau
Feb 2, 1996·Journal of Medicinal Chemistry·R R WexlerP B Timmermans
Aug 1, 1996·Journal of Pharmaceutical Sciences·M T ObermeierR A Morrison
Jan 1, 1999·Bioorganic & Medicinal Chemistry Letters·V SegarraA Martinez
Jul 19, 2002·Organic Letters·Zachary P Demko, K Barry Sharpless
Feb 7, 2003·Current Medicinal Chemistry·Christopher Hulme, Vijay Gore
Jun 29, 2011·Angewandte Chemie·Eelco RuijterRomano V A Orru
Feb 3, 2012·Journal of Medicinal Chemistry·Derek A NicholsYu Chen
Feb 15, 2012·ACS Combinatorial Science·Steven GunawanChristopher Hulme
Mar 23, 2012·Chemical Reviews·Alexander DömlingKan Wang
Nov 20, 2012·Nucleic Acids Research·Matthias WirthWolfgang H B Sauer
Jan 22, 2013·Organic Letters·Ting ZhaoAlexander Dömling
Jan 31, 2013·ChemMedChem·Carlo BallatoreAmos B Smith
Mar 5, 2013·Bioorganic & Medicinal Chemistry Letters·Adam GolebiowskiHagen Schroeter
Jan 24, 2015·Bioorganic & Medicinal Chemistry·Yasuhiro ShimamotoKenichi Akaji
Jan 30, 2015·Bioorganic & Medicinal Chemistry·Pravin PatilAlexander Dömling
Sep 24, 2015·The Journal of Organic Chemistry·Aaron L BrownCraig A Hutton
Jan 1, 2015·European Journal of Organic Chemistry·Tryfon Zarganes-TzitzikasAlexander Dömling

❮ Previous
Next ❯

Citations

Jul 19, 2016·The Journal of Organic Chemistry·Clothilde Le GuenThierry Lequeux
Sep 10, 2016·Organic Letters·Edwin KroonAlexander Dömling
Feb 6, 2017·Frontiers in Medicine·Anna KarawajczykDimitrios Tzalis
Oct 28, 2018·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Pietro CapurroAndrea Basso
Sep 12, 2018·Beilstein Journal of Organic Chemistry·Mohammad A AlnajjarAndreas Hennig
Mar 27, 2021·ChemMedChem·Nefeli GribouraConstantinos G Neochoritis
Apr 5, 2018·Journal of the American Chemical Society·Ruirui GuJean-Marie Lehn
Jun 27, 2018·Organic Letters·Santosh KurhadeAlexander Dömling

❮ Previous
Next ❯

Related Concepts

Trending Feeds

COVID-19

Coronaviruses encompass a large family of viruses that cause the common cold as well as more serious diseases, such as the ongoing outbreak of coronavirus disease 2019 (COVID-19; formally known as 2019-nCoV). Coronaviruses can spread from animals to humans; symptoms include fever, cough, shortness of breath, and breathing difficulties; in more severe cases, infection can lead to death. This feed covers recent research on COVID-19.

Blastomycosis

Blastomycosis fungal infections spread through inhaling Blastomyces dermatitidis spores. Discover the latest research on blastomycosis fungal infections here.

Nuclear Pore Complex in ALS/FTD

Alterations in nucleocytoplasmic transport, controlled by the nuclear pore complex, may be involved in the pathomechanism underlying multiple neurodegenerative diseases including Amyotrophic Lateral Sclerosis and Frontotemporal Dementia. Here is the latest research on the nuclear pore complex in ALS and FTD.

Applications of Molecular Barcoding

The concept of molecular barcoding is that each original DNA or RNA molecule is attached to a unique sequence barcode. Sequence reads having different barcodes represent different original molecules, while sequence reads having the same barcode are results of PCR duplication from one original molecule. Discover the latest research on molecular barcoding here.

Chronic Fatigue Syndrome

Chronic fatigue syndrome is a disease characterized by unexplained disabling fatigue; the pathology of which is incompletely understood. Discover the latest research on chronic fatigue syndrome here.

Evolution of Pluripotency

Pluripotency refers to the ability of a cell to develop into three primary germ cell layers of the embryo. This feed focuses on the mechanisms that underlie the evolution of pluripotency. Here is the latest research.

Position Effect Variegation

Position Effect Variagation occurs when a gene is inactivated due to its positioning near heterochromatic regions within a chromosome. Discover the latest research on Position Effect Variagation here.

STING Receptor Agonists

Stimulator of IFN genes (STING) are a group of transmembrane proteins that are involved in the induction of type I interferon that is important in the innate immune response. The stimulation of STING has been an active area of research in the treatment of cancer and infectious diseases. Here is the latest research on STING receptor agonists.

Microbicide

Microbicides are products that can be applied to vaginal or rectal mucosal surfaces with the goal of preventing, or at least significantly reducing, the transmission of sexually transmitted infections. Here is the latest research on microbicides.

Related Papers

Progress in Medicinal Chemistry
H SinghR K Malhotra
The Journal of Pharmacology and Experimental Therapeutics
E G GROSS, R M FEATHERSTONE
The Journal of Pharmacology and Experimental Therapeutics
E G GROSS, R M FEATHERSTONE
The Journal of Pharmacology and Experimental Therapeutics
E G GROSS, R M FEATHERSTONE
© 2021 Meta ULC. All rights reserved