6 research outputs found
The chemical basis of serine palmitoyltransferase inhibition by myriocin
- Author
- Publication venue
- 'American Chemical Society (ACS)'
- Publication date
- 11/09/2013
- Field of study
Sphingolipids (SLs) are essential components of cellular membranes formed from the condensation of L-serine and a long-chain acyl thioester. This first step is catalyzed by the pyridoxal-5'-phosphate (PLP)-dependent, enzyme serine palmitoyltransferase (SPT) which is a promising therapeutic target. The fungal natural product myriocin is a potent inhibitor of SPT and is widely used to block SL biosynthesis despite a lack of a detailed understanding of its molecular-mechanism. By combining spectroscopy, mass spectrometry, X-ray crystallography, and kinetics, we have characterized the molecular details of SPT inhibition by myriocin. Myriocin initially forms an external aldimine with PLP at the active site, and a structure of the resulting co-complex explains its nanomolar affinity for the enzyme. This co-complex then catalytically degrades via an unexpected 'retro-aldol-like' cleavage mechanism to a C18 aldehyde which in turn acts as a suicide inhibitor of SPT by covalent modification of the essential catalytic lysine. This surprising dual mechanism of inhibition rationalizes the extraordinary potency and longevity of myriocin inhibition.</p
The Chemical Basis of Serine Palmitoyltransferase Inhibition by Myriocin
- Author
- Publication venue
- Publication date
- Field of study
Sphingolipids
(SLs) are essential components of cellular membranes
formed from the condensation of l-serine and a long-chain
acyl thioester. This first step is catalyzed by the pyridoxal-5′-phosphate
(PLP)-dependent enzyme serine palmitoyltransferase (SPT) which is
a promising therapeutic target. The fungal natural product myriocin
is a potent inhibitor of SPT and is widely used to block SL biosynthesis
despite a lack of a detailed understanding of its molecular mechanism.
By combining spectroscopy, mass spectrometry, X-ray crystallography,
and kinetics, we have characterized the molecular details of SPT inhibition
by myriocin. Myriocin initially forms an external aldimine with PLP
at the active site, and a structure of the resulting co-complex explains
its nanomolar affinity for the enzyme. This co-complex then catalytically
degrades via an unexpected ‘retro-aldol-like’ cleavage
mechanism to a C18 aldehyde which in turn acts as a suicide inhibitor
of SPT by covalent modification of the essential catalytic lysine.
This surprising dual mechanism of inhibition rationalizes the extraordinary
potency and longevity of myriocin inhibition
Canada
- Author
- Ahenakew Edward
- Altrows Rona
- Atwood Margaret
- Avison Margaret
- Baker Marie
- Baldwin Robert
- Baldwin Shauna Singh
- Blaser Robin
- Calihoo Robert
- Clark Joan
- Clarke George Elliott
- Coady Lynn
- Cohen Leonard
- Coupland Douglas
- Culleton Beatrice
- Day Frank Parker
- Diana Chlebek
- E. Pauline Johnson
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- Ellwood Ray
- Engel Marian
- Francis Marvin
- Fraser Brad
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- Herring Frances
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- Hopkinson Nalo
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- Johnston Wayne
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- Laurence Margaret
- Lee Sky
- Lowther Pat
- MacLeod Alistair
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- Marian Butler
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- Murrell John
- Neilson Shane
- Ondaatje Michael
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- Ross Sinclair
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- Skaay of the Qquuna Qiighawaay
- Souster Raymond
- Stafford O'Neil illus Bernard Low
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- Vanderhaeghe Guy
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- Watson Sheila
- Publication venue
- 'SAGE Publications'
- Publication date
- Field of study
Poetry
- Author
- Andrusyshyn Larissa
- Armstrong Tammy
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- Publication venue
- 'University of Toronto Press Inc. (UTPress)'
- Publication date
- Field of study
Canada
- Author
- A. Amprimoz
- A. Amprimoz
- A. Blott
- A. Boutelle
- A. Brodie
- A. Feder
- A. Gandolfo
- A. Purdy
- A. Roche
- A.C. Stewart
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- A.E. Davidson
- A.W. Riley
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- Alianak Hrant
- Allen Robert
- Amprimoz Alexandre
- Andrus David
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- Aquin Hubert
- Ardies Tom
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- Atwood Margaret
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- Austin Don
- Avery Martin
- Avison Margaret
- Avison Margaret
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- Canadian
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- Cohen Matt
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- D. Barbour
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- D. Bessai
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Canada
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- A. D. Armitage
- A. Dawe
- A. Mandel
- A. Mitcham
- A. Yandle.
- A.Mitcham
- Allen Dale.
- Ammeter A.E.
- Amprimoz Alexandre.
- Annand Alan Mark.
- Aspler Tony.
- Atkinson Steve.
- Atwood Margaret.
- B. Bailey
- B. Cameron
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- B. Lever
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- Bessette Gérard.
- Bishop Billy.
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- Blodgett E.D.
- Bolechala Josephine.
- Bolen Dennis E.
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- Brenner David Norman.
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- Gustafson Ralph.
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- Knister Raymond.
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- Marshall Tom.
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- McClung Nellie.
- McCourt Edward.
- McIntyre Anna.
- McKay Don.
- McKay Jean.
- McLeod Joseph.
- McNamara Eugene.
- McWhirter George.
- Meilleur Peter
- Metcalf John.
- Metcalf John.
- Michel Tremblay
- Michel Tremblay
- Michel Tremblay
- Miller Angela.
- Mills John.
- Mills Margaret.
- Misfeldt James.
- Mitchell Jeannine.
- Mitchell Marsha.
- Moore Brian.
- Moore Brian.
- Morton Colin.
- Moyer Carolyn.
- Mundwiler Leslie.
- Munro Alice.
- Murdie Donna Haggarty.
- Myers Martin.
- Newlove John.
- Newman Peter C.
- Nicol Eric.
- Nicol James W.
- Nowlan Alden.
- O'Neill Paul.
- O.H.T. Rudzik
- Oates Joyce Carol.
- Ohm Vibeke.
- Ondaatje Michael.
- P-A. Arcand
- P. Grant
- P. Kogan
- P. Oliver .
- P. Stuewe
- P. Stuewe
- Pacey Desmond.
- Page P.K.
- Palomba Lauro.
- Pass John.
- Paterson Leonard.
- Pendergrast William.
- Percy H.R.
- Perkin J.R.C.
- Persky Stan.
- Persky Stan.
- Peterson Leonard.
- Peterson Phyllis Lee.
- Pittman Alphonsus.
- Plaskett John.
- Poirier R.A.
- Powell Derek Reid.
- Powning Beth.
- Pratt E.J.
- Purdy A.
- Purdy Al.
- R . Gool.
- R. Binns
- R. Daniells
- R. Davies
- R. Diotte
- R. Endres
- R. Endres.
- R. Gibbs
- R. Gustafson
- R. Hopkins
- R. Kalman.
- R. Knister
- R. Knister
- R. Lecker
- R. Mathews
- R. Plant
- R. Stuart
- R. Stuewe
- R. Sullivan
- R. Wyatt
- R.C. Castro
- R.G. Landon
- R.H. Fossum
- R.K. Wilcox
- R.Stuart
- Rae Donna.
- Randall Margaret.
- Rapoport Janis.
- Reaney James.
- Reaney James.
- Reid John.
- Reigo Ants.
- Richards David
- Richler Mordecai.
- Richler Mordecai.
- Rikki
- Ringwood Gwen
- Ringwood Gwen Pharis.
- Roberts Sir Charles G. D.
- Roberts Sir Charles G. D.
- Robertson Marjorie.
- Roch Carrier
- Rodgers Joan.
- Rohmer Richard.
- Rohmer Richard.
- Rooke Leon.
- Rosqui Carolyn.
- Ross Irwin.
- Ross James.
- Rosta Helen J.
- Rowe Terry.
- Roy Gabrielle.
- Ryga George.
- S. Nagarajan
- S. Scobie
- S. Souchotte
- S. Swan
- S.Djwa
- S.G. Mullins
- S.M. Beckow
- Salutin Rick
- Sarah Robyn.
- Schackleton Doris.
- Schoemperlen Diane.
- Scott Anne
- Scott Duncan Campbell.
- Sears Dennis Patrick.
- Seitz Mary Ann.
- Shaffer Ivan.
- Sheinsky B.
- Siegel J.H.
- Siegel Jay H.
- Simpson Leo.
- Sinclair Gordon.
- Sister C. Kelly
- Skelton Robin.
- Slabotsky David.
- Smith A.J.M.
- Smith Michael.
- Smith Rod.
- Smyth Donna E.
- Sorestad Glen.
- Soulikias Constance Whittaker.
- Stambaugh Sara.
- Stange Ken.
- Stanley George.
- Stegner Wallace.
- Stevens Peter.
- Stevenson David.
- Stewart Cherie.
- Story Alice.
- Summerfield Edith.
- Sutherland Fraser.
- Sutherland Fraser.
- Symons R.D.
- Szanto G.H.
- Szohner Gabriel.
- T. Angus.
- T. Marshall
- Taafe Gerald.
- Tamminga Frederick W.
- Tata Saam.
- Teitel Jay.
- Tens Johnny.
- Thayer Nancy.
- Thibaudeau Colleen.
- Thibaudeau Colleen.
- Thomas Audrey.
- Thomas Audrey.
- Thomas John.
- Thompson Henrietta Moser.
- Thompson Kent.
- Totzke Stephen.
- Trail Catharine Parr.
- Tremblay Michel.
- Trower Peter Gerrard.
- Truss Jan.
- Turnbull Robert O.
- Twieg B.J.
- V. Frankel
- V. Miner
- Vanderhaege Guy.
- Victor-Lévy Beaulieu
- Voaden Herman.
- Voaden Herman.
- W.Francis
- W.H. New
- W.H. New
- Waddington Miriam.
- Waddington Miriam.
- Wade Bryan.
- Walsh George Johnston.
- Watt F.W.
- Watts Enos D.
- Webb Phyllis.
- Weinzweig Helen.
- Wetmore Andrew.
- White Marilyn.
- Wilson Ethel.
- Wiseman Adele.
- Woodcock George.
- Wright Richard B.
- Wynand Derk.
- Yates J.
- Yates J. Michael.
- Zend Robert.
- Publication venue
- 'SAGE Publications'
- Publication date
- Field of study