Design and Synthesis of Potent “Sulfur-Free” Transition State Analogue Inhibitors of 5′-Methylthioadenosine Nucleosidase and 5′-Methylthioadenosine Phosphorylase

Alistair I. Longshaw; Florian Adanitsch; Jemy A. Gutierrez; Gary B. Evans; Peter C. Tyler; Vern L. Schramm

doi:10.1021/jm100898v

Design and Synthesis of Potent “Sulfur-Free” Transition State Analogue Inhibitors of 5′-Methylthioadenosine Nucleosidase and 5′-Methylthioadenosine Phosphorylase

Journal of Medicinal Chemistry ◽

10.1021/jm100898v ◽

2010 ◽

Vol 53 (18) ◽

pp. 6730-6746 ◽

Cited By ~ 30

Author(s):

Alistair I. Longshaw ◽

Florian Adanitsch ◽

Jemy A. Gutierrez ◽

Gary B. Evans ◽

Peter C. Tyler ◽

...

Keyword(s):

Transition State ◽

Design And Synthesis ◽

Methylthioadenosine Phosphorylase ◽

Transition State Analogue ◽

Free Transition ◽

Transition State Analogue Inhibitors

Targeting the Polyamine Pathway with Transition-State Analogue Inhibitors of 5‘-Methylthioadenosine Phosphorylase

Journal of Medicinal Chemistry ◽

10.1021/jm0306475 ◽

2004 ◽

Vol 47 (12) ◽

pp. 3275-3281 ◽

Cited By ~ 37

Author(s):

Gary B. Evans ◽

Richard H. Furneaux ◽

Vern L. Schramm ◽

Vipender Singh ◽

Peter C. Tyler

Keyword(s):

Transition State ◽

Methylthioadenosine Phosphorylase ◽

Transition State Analogue ◽

Transition State Analogue Inhibitors

The Synthesis of N-Ribosyl Transferase Inhibitors Based on a Transition State Blueprint

Australian Journal of Chemistry ◽

10.1071/ch04112 ◽

2004 ◽

Vol 57 (9) ◽

pp. 837 ◽

Cited By ~ 7

Author(s):

Gary B. Evans

Keyword(s):

Transition State ◽

Enzyme Inhibitors ◽

Processing Enzymes ◽

Design And Synthesis ◽

Therapeutic Uses ◽

Transition State Analogue ◽

Transition State Analogue Inhibitors ◽

State Analysis

A quarter of a century ago transition state analysis and transition state analogue design promised the prospect of extraordinarily potent enzyme inhibitors. The present overview describes the transition state analysis of a variety of N-ribosyl transferases, the design and synthesis of extremely powerful transition state analogue inhibitors of these nucleoside processing enzymes, and their current therapeutic uses and potentials.

Transition state analogue inhibitors of human methylthioadenosine phosphorylase and bacterial methylthioadenosine/S-adenosylhomocysteine nucleosidase incorporating acyclic ribooxacarbenium ion mimics

Bioorganic & Medicinal Chemistry ◽

10.1016/j.bmc.2012.07.006 ◽

2012 ◽

Vol 20 (17) ◽

pp. 5181-5187 ◽

Cited By ~ 10

Author(s):

Keith Clinch ◽

Gary B. Evans ◽

Richard F.G. Fröhlich ◽

Shivali A. Gulab ◽

Jemy A. Gutierrez ◽

...

Keyword(s):

Transition State ◽

Methylthioadenosine Phosphorylase ◽

Transition State Analogue ◽

Transition State Analogue Inhibitors

TRANSITION STATE ANALOGUE INHIBITORS OF METHYLTHIOADENOSINE PHOSPHORYLASE: TOWARDS NEW CANCER THERAPEUTICS

XXIst International Carbohydrate Symposium 2002 ◽

10.1100/tsw.2002.485 ◽

2002 ◽

Author(s):

Gary B. Evans ◽

Richard H. Furneaux ◽

Vern L. Schramm ◽

Peter C. Tyler

Keyword(s):

Transition State ◽

Cancer Therapeutics ◽

Methylthioadenosine Phosphorylase ◽

Transition State Analogue ◽

Transition State Analogue Inhibitors

ChemInform Abstract: Design and Synthesis of New Transition-State Analogue Inhibitors of Aspartate Transcarbamylase.

Chemischer Informationsdienst ◽

10.1002/chin.198609209 ◽

1986 ◽

Vol 17 (9) ◽

Author(s):

G. K. FARRINGTON ◽

A. KUMAR ◽

F. C. WEDLER

Keyword(s):

Transition State ◽

Aspartate Transcarbamylase ◽

Design And Synthesis ◽

Transition State Analogue ◽

Transition State Analogue Inhibitors

Picomolar Transition State Analogue Inhibitors of Human 5‘-Methylthioadenosine Phosphorylase and X-ray Structure with MT-Immucillin-A†

Biochemistry ◽

10.1021/bi0358420 ◽

2004 ◽

Vol 43 (1) ◽

pp. 9-18 ◽

Cited By ~ 44

Author(s):

Vipender Singh ◽

Wuxian Shi ◽

Gary B. Evans ◽

Peter C. Tyler ◽

Richard H. Furneaux ◽

...

Keyword(s):

Transition State ◽

X Ray ◽

Methylthioadenosine Phosphorylase ◽

Transition State Analogue ◽

Transition State Analogue Inhibitors

Second Generation Transition State Analogue Inhibitors of Human 5‘-Methylthioadenosine Phosphorylase

Journal of Medicinal Chemistry ◽

10.1021/jm050269z ◽

2005 ◽

Vol 48 (14) ◽

pp. 4679-4689 ◽

Cited By ~ 41

Author(s):

Gary B. Evans ◽

Richard H. Furneaux ◽

Dirk H. Lenz ◽

Gavin F. Painter ◽

Vern L. Schramm ◽

...

Keyword(s):

Transition State ◽

Second Generation ◽

Methylthioadenosine Phosphorylase ◽

Transition State Analogue ◽

Transition State Analogue Inhibitors

Entropy-Driven Binding of Picomolar Transition State Analogue Inhibitors to Human 5′-Methylthioadenosine Phosphorylase

Biochemistry ◽

10.1021/bi201321x ◽

2011 ◽

Vol 50 (47) ◽

pp. 10408-10417 ◽

Cited By ~ 16

Author(s):

Rong Guan ◽

Meng-Chiao Ho ◽

Michael Brenowitz ◽

Peter C. Tyler ◽

Gary B. Evans ◽

...

Keyword(s):

Transition State ◽

Methylthioadenosine Phosphorylase ◽

Transition State Analogue ◽

Transition State Analogue Inhibitors

Faculty Opinions recommendation of L-Enantiomers of transition state analogue inhibitors bound to human purine nucleoside phosphorylase.

Faculty Opinions – Post-Publication Peer Review of the Biomedical Literature ◽

10.3410/f.1097544.553622 ◽

2008 ◽

Author(s):

Wayne Guida

Keyword(s):

Transition State ◽

Purine Nucleoside Phosphorylase ◽

Purine Nucleoside ◽

Nucleoside Phosphorylase ◽

Transition State Analogue ◽

Transition State Analogue Inhibitors

A new class of C-nucleoside analogues. 1-(S)-aryl-1,4-dideoxy-1,4-imino-D-ribitols, transition state analogue inhibitors of nucleoside hydrolase

Tetrahedron Letters ◽

10.1016/s0040-4039(00)79290-2 ◽

1993 ◽

Vol 34 (45) ◽

pp. 7213-7216 ◽

Cited By ~ 51

Author(s):

Benjamin A. Horenstein ◽

Roger F. Zabinski ◽

Vern L. Schramm

Keyword(s):

Transition State ◽

Nucleoside Analogues ◽

New Class ◽

Nucleoside Hydrolase ◽

Transition State Analogue ◽

Transition State Analogue Inhibitors