Synthesis of a potent 5'-methylthioadenosine/S-adenosylhomocysteine (MTAN) inhibitor

Vivekanand P Kamath; Jainwen Zhang; Philip E Morris Jr; Y Sudhakar Babu

doi:10.1016/j.bmcl.2006.02.029

Synthesis of a potent 5'-methylthioadenosine/S-adenosylhomocysteine (MTAN) inhibitor

Bioorg Med Chem Lett. 2006 May 15;16(10):2662-5. doi: 10.1016/j.bmcl.2006.02.029. Epub 2006 Feb 28.

Authors

Vivekanand P Kamath¹, Jainwen Zhang, Philip E Morris Jr, Y Sudhakar Babu

Affiliation

¹ BioCryst Pharmaceuticals Inc., 2190 Parkway Lake Drive, Birmingham, AL 35244, USA.

PMID: 16504506
DOI: 10.1016/j.bmcl.2006.02.029

Abstract

MTAN has been known to occur in a variety of bacterial cell types. Due to the evolution of bacterial strains which are resistant to some of the most powerful antibiotics there has been a renewed interest in the development of novel anti-microbial agents. Presented herein is a synthesis of a potent MTAN inhibitor, namely 2-amino-4-[5-(4-amino-5H-pyrrolo[3,2-d]pyrimidin-7-yl)-3,4-dihydroxypyrrolidin-2-ylmethylsulfanyl]-butyric acid (1).

MeSH terms

Butyrates / chemical synthesis*
Butyrates / pharmacology*
Deoxyadenosines / antagonists & inhibitors*
S-Adenosylhomocysteine / antagonists & inhibitors*
Spectrophotometry, Ultraviolet
Thionucleosides / antagonists & inhibitors*

Substances

2-amino-4-(5-(4-amino-5H-pyrrolo(3,2-d)pyrimidin-7-yl)-3,4-dihydroxypyrrolidin-2-ylmethylsulfanyl)butyric acid
Butyrates
Deoxyadenosines
Thionucleosides
5'-methylthioadenosine
S-Adenosylhomocysteine