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Clark W. Still Career in Review. Department of Chemistry, University of Ottawa March 17 th , 2009 By Anik Michelle Chartrand. Who Is He ?. 1946 - B orn in Augusta, Georgia 1964 - Graduated from Winter Haven High School in Polk Country, FL 1969- B.Sc. At Emory University

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slide1

Clark W. Still

Career in Review

Department of Chemistry, University of Ottawa

March 17th, 2009

By Anik Michelle Chartrand

who is he
Who Is He ?
  • 1946 - Born in Augusta, Georgia
  • 1964 - Graduated from Winter Haven High

School in Polk Country, FL

  • 1969- B.Sc. At Emory University
  • 1972- Ph.D. At Emory University – Advisor was David Goldsmith
  • 1973- Postdoc at Princeton University (computer related)
  • 1974/75- Postdoc at Columbia University with Gilbert Stork
  • 1975/76- Professor at Vanderbilt University in Nashville, TN
  • 1977 to 98 - Professor at Columbia University in NY, NY
  • 1999 – Professor Emeritus, Columbia University in NY, N
his graduate work 1969 72
His Graduate Work (1969-72)
  • Diborane Reductions of Oxygen Heterocycles
  • Hydroboration-Oxydation Products of Oxygen Heterocycles

W. C. Still and D.J. Goldsmith, J. Org. Chem., 1970, 35 (7), 2282

his graduate work 1969 721
His Graduate Work (1969-72)
  • The decarboxylative elimination reaction of β,γ- epoxyacids
  • to make allylic alcohols
  • Bicyclic Intermediate for Trichothecane Synthesis
  • Exploitation of an Enolate as a Protecting Group
  • Tandem sequence involving bis alkylation

Still, W.C.; Lewis, A.J.; Goldsmith D.; Tetrahedron Letters, 1971,18, 1421

Still, W.C.; Lewis, A.J.; Goldsmith D.; Tetrahedron Letters, 1973,48, 4807

his graduate work 1974 75
His Graduate Work (1974-75)

Most of his work with Prof. Stork concentrated of the formation of Gibberellic Acids B-C-D ring:

  • Reductive cyclization of Ethynylketones
  • Unusual regiospecificity in the enolization of a ketone as the result of a difference
  • in energy to achieve the best overlap of an alpha hydrogen

Stork, G.; Boeckman, R.K. Jr..; Taber, D.F.; Still W.C. Singh, J. ,JACS, 1979, 101 (23) 7107

Stork, G.; Still W.C. Singh, J., Tetrahedron Letters, 1979, 52, 5077

slide7

Independent Researcher

Vanderbilt University

Columbia University

his work at vanderbilt university 1975 76
His Work at Vanderbilt University (1975-76)
  • Organocuprates and the development of a new highly selective stereoselective alkylation agent to produce axial alcohols

“ In contrast to the numerous highly stereoselective reducing agents which have

been developed, the ability of reagents for the addition of unhindered alkyl

nucleophiles to ketones with high stereoselectivity is limited.”

  • Conjugate Addition of trimetylsilyllithium – Axial addition is highly favoured

Macdonald, T.L.; Still, W.C.; JACS, 1975, 97(18), 5280 & Still, W.C., J. Org. Chem., 1976, 41(18), 3063

his work at vanderbilt university 1975 761
His Work at Vanderbilt University (1975-76)
  • AllyloxyCarbanions:
    • Cyclization to vinyl oxetans via allyloxycarbanions :
    • Selective fomation of the more strained oxetane as long
    • as the addition produces the cis ring juncture

Still C.W., Tetrahedron Letters, 1976, 25, 2115 & Still, W.C.; Macdonald, T.L.; J. Org. Chem., 1976, 41(22), 3620.

his work at vanderbilt university 1975 762
His Work at Vanderbilt University (1975-76)
  • Claisen Variant:
  • Tin chemistry (stannylation/destannylation)
    • α-AlkoxyOrganolithium Reagents

Still, C.W.; Schneider, M.J., JACS, 1977,99(3), 948 & Still, C.W., JACS, 1978, 100 (5), 1481

his work at vanderbilt university 1975 763
His Work at Vanderbilt University (1975-76)
  • Tri-alkyl tin anions undergo high yield conjugate addition to α,β-enones to give
  • the regiospecificenolate

42

40

41

  • Alkylstannanes are smoothly oxidized by chromic anhydride/pyridine to the
  • corresponding ketone
  • Alkylation and oxidation – efficient dialkylativeenone transposition

Still, C.W., JACS, 1977, 99(14), 4836

columbia university 1977 1998
Columbia University (1977-1998)
  • Anionic [2,3]-sigmatropic rearrangements

Still, C.W.; McDonald J.H. III; Collum, D.B.; Mitra, A., Tetrahedron Letters, 1979, 7, 593 &

Still, C.W.; Kahn, M.; Mitra, A., J. Org. Chem., 1978, 43(14), 2923

columbia university 1977 19981
Columbia University (1977-1998)
  • Rapid Chromatographic Technique for Preparative Separation of
  • moderate resolution
    • “ We have recently developed a substantially faster technique
    • for the routine purification of a products which we call
    • flash chromatography.”
  • Monensin – Polyether antibiotic and naturally occurring ionophore
  • 17 asymmmetric centers, 26 carbon backbone
  • Theoretically 131 072 stereoisomers can exist

1) Still, C.W.; Kahn, M.; Mitra, A., J. Org. Chem., 1978, 43(14), 2923 2) Still, W. C.; Dongwei, J. Org. Chem., 1988,53, 4643 3) Still, W.C.; MacDonald, J.H.III; Collum, D.B.; JACS, 1980, 102(6), 2117 4) Still, W.C.; MacDonald, J.H.III; Collum, D.B.; JACS, 1980,102(6), 2118 5)Still, W.C.; MacDonald, J.H.III; Collum, D.B.; JACS, 1980, 102(6), 2120

columbia university 1977 19982
Columbia University (1977-1998)
  • Direct Synthesis of Z-unsaturated esters; a useful modification of the
  • Horner-Emmons Olefination

Horner-Wadsworth-Emmons

Still – Gennari Modification

Still, W.C., JACS, 1979, 101(9), 2493 & Adams, M.A.; Nakanishi, K.; Still, W.C.; Arnold, E.V.; Clardy, J.; Persoons, C.J.; JACS, 1979, 101(9), 2495

z trisubstituted allylic alcohols via the wittig reaction
Z-trisubstitutedAllylic Alcohols via the Wittig Reaction

Schlosser, M; Christmann, K.F. Angew. Chem. Intl, Ed., 1966, 5(1), 126 &

Schlosser, M; Christmann, K.F,; Muller, G., Angew. Chem. Intl, Ed., 1966, 5 (17), 667 &

Corey, E.J.; Yamamoto, H.; JACS,1970, 92(1), 226

z trisubstituted allylic alcohols via the wittig reaction1
Z-trisubstitutedAllylic Alcohols via the Wittig Reaction
  • Noβ-oxidoYlide intermediate or n-BuLi required

α

Counterion effect

Phosphoniumfluoroborate

Vs

Phosphonium halide

α ‘

α-santalol

Sreekumar, C.; Darst, K.P.; Still, W.C., J. Org. Chem, 1980, 45(21), 4260

columbia university 1977 19983
Columbia University (1977-1998)
  • Dichlorocarbenecyclopropanation of allylic alcohols:

This is a Simmons-Smith

equivalent that works

well in acyclic systems

  • Synthesis of Alternating Hydroxy- and Methyl-Substituted Hydrocarbons by
  • Oxymercuration of Cyclopropylcarbinols.

Mohamadi, F.; Still, W.C., Tetrahedron Letters, 1986, 27(8), 893 &

Collum, D.B.; Still, W.C., Mohamadi, F., JACS,1986, 108(8), 2094

columbia university 1977 19984
Columbia University (1977-1998)
  • A highly stereoselective synthesis of trans epoxides via arsoniumYlides

High stereoselectivity

for trans epoxide ≥ 50:1

  • Remote 1,3-, 1,4-,and 1,5- asymmetric induction. A stereoselective approach to acyclic
  • diols via Cyclic Hydroboration

Still, W.C.; Novack, V. J., JACS,1981, 103(5), 1283 &

Still , W.C..; Darst, K.P., JACS,1980, 1021(24), 7385

columbia university 1977 19985
Columbia University (1977-1998)
  • Synthesis of MacrocyclicTrichothecanoids: Baccharin B5 and Roridin E

85

86

87

88

  • Chemical consequence of conformation in macrocyclic compounds. An effective approach
  • to remote asymmetric induction.

Still, W.C.; Gennari, C.; Noguez, J.A..; Pearson, D.A., JACS,1984, 106(1), 260 &

Still, W.C.; Galynker, I., Tetrahedron,1981, 37 (23), 3981

macrocycles
Macrocycles
  • Stereochemical control - acyclic and macrocyclic natural products rely on some form of
  • absolute stereochemical control to set up remote diastereometric relationship
      • Readily available enantiomerically pure S.M.
      • Resolution of an intermediate
      • Asymetric induction by enantiomerically pure reagent
  • Still’s alternative – pre-existing substrate chirality, which may be quite distant from the
  • reaction site, to direct the stereoselectivity of the reaction.

Conformations – Transannular non bonded repulsions and high-energy torsional

arrangements must be minimized

Still, W.C.; Galynker, I., Tetrahedron,1981, 37(23), 3981

9 membered rings
9-Membered Rings

Still, W.C.; Galynker, I., Tetrahedron, 1981, 37 (23), 3981

peripheral vs antiperipheral attack
Peripheral vsAntiperipheral Attack
  • 3D Structure – sp2 centers are perpendicular to the plane of the ring

Cis-cyclohexene

Cis- cyclooctene

Cis- cyclodecene

  • 2 faces of π-system are sterically different
  • Peripheral attack preferred

Still, W.C.; Galynker, I., Tetrahedron, 1981, 37 (23), 3981

periplanone b total synthesis and structure of the sex excitant pheromone of the american cockroach
Periplanone B- Total synthesis and structure of the Sex Excitant Pheromone of the American Cockroach
  • Female species of Periplanetaamericana, the American
  • Cockroach.
  • In the early 70’s Persoons et al. Isolated two extremely active compounds, periplanones-A (-20 pg) and -B (-200 pg).
  • Periplanone-B was characterized spectrally and
  • tentatively assigned a germacranoid structure.
  • Still reported highly stereoselective syntheses of three of the four possible diastereomers.

Still, W.C., JACS, 1979, 101(9), 2493

periplanone b first diastereomer
Periplanone B – First Diastereomer

C-5 and C-6 Diaxial coupling (10Hz);

C-7 and C-8 trans coupling (16 Hz)

Still, W.C., JACS, 1979, 101(9), 2493 &

Adams, M.A.; Nakanishi, K.; Still, W.C.;

Arnold, E.V.; Clardy, J.; Persoons, C.J.; JACS,1979, 101(9), 2495

periplanone b stereocontrol approach
Periplanone B – Stereocontrol Approach

X

Peripheral

Attack

  • Diastereomers synthesis:
    • 1-5 Cyclodecadienes have a well defined conformation
    • Olefinic linkage perpendicular to plane of ring.
    • Attack from less hindered peripheral face of the π system

Still, W.C., JACS, 1979, 101(9), 2493 &

Adams, M.A.; Nakanishi, K.; Still, W.C.; Arnold, E.V.; Clardy, J.; Persoons, C.J.; JACS,1979, 101(9), 2495

periplanone b first diastereomer1
Periplanone B – First Diastereomer

Spectral comparison with

authentic Periplanone-B

concludes they are

Unidentical

periplanone b first diastereomer2
Periplanone B – First Diastereomer

First Disatereomer

  • 300-MHz NMR strongly suggest :
    • Only difference is the configuration of the isopropyl group.
      • Pseudo-axial in X: (J7-8 = 5, J8-9a = 7.5, J8-9b= 2 Hz)
      • Pseudo-equatorial (Periplanone B) : (J7-8 = 10, J8-9a = 10, J8-9b= 5.5 Hz

Still, W.C., JACS, 1979, 101(9), 2493 &

Adams, M.A.; Nakanishi, K.; Still, W.C.; Arnold, E.V.; Clardy, J.; Persoons, C.J.; JACS, 1979, 101(9), 2495

periplanone b second diastereomer
Periplanone B – Second Diastereomer
  • NMR of 116 is very different than Periplanone B
    • Transannular -O- interaction is replaced by a more severe -CH2- interaction

Still, W.C., JACS, 1979,101(9), 2493 &

Adams, M.A.; Nakanishi, K.; Still, W.C.; Arnold, E.V.; Clardy, J.; Persoons, C.J.; JACS,1979, 101(9), 2495

periplanone b third diastereomer
Periplanone B -Third Diastereomer
  • Construction of the stereoisomeric C-2 – C-3 cisepoxide:
    • Desired epoxide is the more hindered one.

Disfavoured

Antiperipheral attack

needed

favoured

peripheral attack

NOT WANTED

  • Alternate tactic was chosen – construction of the C-5 – C-7 conjugated diene :

New conformation exposes opposite face to peripheral attack

Still, W.C., JACS,1979, 101(9), 2493 &

Adams, M.A.; Nakanishi, K.; Still, W.C.; Arnold, E.V.; Clardy, J.; Persoons, C.J.; JACS, 1979, 101(9), 2495

periplanone b third diastereomer1
Periplanone B -Third Diastereomer
  • Comparison of (±) – 121 with Periplanone–B showed they were identical

Still, W.C., JACS, 1979, 101(9), 2493 &

Adams, M.A.; Nakanishi, K.; Still, W.C.; Arnold, E.V.; Clardy, J.; Persoons, C.J.; JACS,1979,101(9), 2495

columbia university 1977 19986
Columbia University (1977-1998)
  • An internal Coordinate Monte Carlo method for searching conformational Space
  • Random Search for finding the low-energy
  • conformations of molecules
  • Was the first to create a software available and
  • and fairly easy to use for the general public

Chang, G.; Guida, W.C.; Still, W.C., JACS, 1989, 111 (8), 3075

slide33

Columbia University (1977-1998)

  • Complex Synthetic chemical libraries indexed with molecular tags
  • A new generation of Fluorescent chemosensors demonstrate improved analyte detection
  • sensitivity and photobleaching resistance.

Nestler, H.P.; Barlett, P.A.; Still, W.C., J. Org. Chem., 1994, 59(17), 4723 &

Ohlmeyer, M.H.J.; Swanson, R.N.; Dillard, L.W.; Reader, J.C.;Asouline, G.;Kobayashi, R.; Wigler, M.;Still, W.C., Proc. Natl. Acad. Sci. USA,

1993, 90(23), 10922 & Rothman, J.H.; Still, W.C., Bioorg.& Med. Chem. Letters, 1999, 9(4), 509 &

Chen, C.T.; Wagner, H.; Still, W.C., Science, 1998, 279 (5352), 851

complex synthetic chemical libraries indexed with molecular tags
Complex Synthetic Chemical Libraries Indexed with Molecular Tags
  • Spaciallysegrated arrays
      • Only small libraries
  • Multivalent synthesis methods
      • Moderate complexity library is produced
      • Pooling of multiple reagents during synthesis
      • Pool is identified to have interesting properties
      • Resynthesized with lower and lower complexity till one compound is identified
      • NOT practical for construction of massive libraries.
  • Split synthesis
      • On solid particles (ex. Beads)
      • Each bead has a product from a single reaction sequence bound to it
      • Selection of a bead with desirable property followed by ID of substrate by analytic method.
      • Only for compounds that can be readily elucidated by micro scale sequencing.
  • Co-synthesis method
      • Co-synthesis of a sequencable tag encoding the steps and reagents used in each step.
      • Oligonucleotide and oligopeptide tags are used
      • Problem = tag is labile, can associate selectively with biological receptors.

Ohlmeyer, M.H.J.; Swanson, R.N.; Dillard, L.W.; Reader, J.C.;Asouline, G.;Kobayashi, R.; Wigler, M.;Still, W.C., Proc. Natl. Acad. Sci. USA, 1993, 90(23), 10922

complex synthetic chemical libraries indexed with molecular tags1
Complex Synthetic chemical libraries indexed with molecular tags
  • Chemically encoded combinatorial library
    • Synthesis on microsphere beads (like in split method)
    • Each step tagging molecules are attached to the beads
    • Encodes both the step number and reagent used in that step = Binary record
    • No co-synthesis required (tags not connected)
    • 20 tags = 1 048 576 different syntheses

Ohlmeyer, M.H.J.; Swanson, R.N.; Dillard, L.W.; Reader, J.C.;Asouline, G.;Kobayashi, R.; Wigler, M.;Still, W.C., Proc. Natl. Acad. Sci. USA,

1993, 90(23), 10922

result analysis
Result Analysis

Peptide library beads stained with mAb 9E10.

GC of tags from EQKLISEEDLGGGG-Bead

Ohlmeyer, M.H.J.; Swanson, R.N.; Dillard, L.W.; Reader, J.C.;Asouline, G.;Kobayashi, R.; Wigler, M.;Still, W.C., Proc. Natl. Acad. Sci. USA,

1993, 90(23), 10922

general method for molecular tagging of encoded combinatorial libraries
General Method for Molecular Tagging of Encoded Combinatorial Libraries
  • Requires no particular tag-attaching functional group other than what already
  • makes up the polymer matrix
  • New tagging reagent = tag plus linker

Nestler, H.P.; Barlett, P.A.; Still, W.C., J. Org. Chem., 1994, 59(17), 4723

fluorescent sequence selective peptide detection by synthetic small molecules
Fluorescent, Sequence-Selective Peptide Detection by Synthetic Small molecules
  • Chemosensors are small molecules that signal the presence of analytes, and typically have
  • two components:
      • Receptor – site that selectively binds an analyte
      • Redout mechanism – signals binding.
  • Chemosensor for tripeptides in CHCl3.
  • Function as synthetic analogs of the
  • antigen-binding site of immunoglobulins

FET signal transduction system

Rothman, J.H.; Still, W.C., Bioorg.& Med. Chem. Letters, 1999, 9(4), 509 &

Chen, C.T.; Wagner, H.; Still, W.C., Science, 1998, 279 5352), 851

chemosensors
Chemosensors

Chemosensor A

Chemosensor B

Dabcyl N-hydrosuccinamide ester

Q = COC6H4N=NC6H4NMe2

F = (CH2)2NH-SO2C10H6NMe2

Dansylsulfonamide of ethanolamine

fluorescent sequence selective peptide detection by synthetic small molecules1
Fluorescent, Sequence-Selective Peptide Detection by Synthetic Small molecules

Fluorescence spectra of chemosensor A and B with Peptides P1 and P2

  • Demonstrate the sequence selective optical detection of peptides
  • By small molecules chemosensor
  • Can be extended to solid state libraries

Rothman, J.H.; Still, W.C., Bioorg.& Med. Chem. Letters, 1999, 9(4), 509 &

Chen, C.T.; Wagner, H.; Still, W.C., Science, 1998, 279 (5352), 851

new fluorencent chemosensors with improved photobleaching resistance
New FluorencentChemosensors with Improved Photobleaching Resistance
  • Photobleaching: is the photochemical destruction of a fluorophore.
      • Major problem with chemosensors that report binding via fluorescence trough UV
  • FRET ( fluorescence resonance energy transfer) interaction
      • The level of fluorescence that escapes quenching is proportional
      • to the binding strength
      • Photobleaching is a significant source of detection error.

Rothman, J.H.; Still, W.C., Bioorg.& Med. Chem. Letters, 1999, 9(4), 509 &

Chen, C.T.; Wagner, H.; Still, W.C., Science, 1998, 279 (5352), 851

new fluorencent chemosensors with improved photobleaching resistance1
New FluorencentChemosensors with Improved Photobleaching Resistance

Dansylfluorofore moiety

Known to undergo photobleaching

Rothman, J.H.; Still, W.C., Bioorg.& Med. Chem. Letters, 1999, 9(4), 509 &

Chen, C.T.; Wagner, H.; Still, W.C., Science, 1998, 279 (5352), 851

dansyl vs acridone moiety
DansylvsAcridone Moiety
  • Replacement of the dansylfluorophore moiety with an acridone derivative

Rothman, J.H.; Still, W.C., Bioorg.& Med. Chem. Letters, 1999, 9(4), 509 &

Chen, C.T.; Wagner, H.; Still, W.C., Science, 1998, 279 (5352), 851

new fluorencent chemosensors with improved photobleaching resistance2
New FluorencentChemosensors with Improved Photobleaching Resistance

Receptor binding saturation experiment.

  • Receptor is now more resistant to fluorophorephotobleaching.
  • No significant change in binding saturation characteristics
  • Acridone exhibits increased fluorescence upon binding

Rothman, J.H.; Still, W.C., Bioorg.& Med. Chem. Letters, 1999, 9(4), 509 &

Chen, C.T.; Wagner, H.; Still, W.C., Science, 1998, 279 (5352), 851

conclusion
Conclusion
  • Still was clearly ahead of his time
    • - Total synthesis - Methodology
    • - Computational chemistry - Chemical biology etc..
  • 3 most cited papers (from a total of 190 publications):
  • 1) Still W.C.; Kahn M., Mitra A., Rapid Chromatographic Technique for Preparative
  • Separations with Moderate Resolutions, J. Org. Chem., 1978, 43(14), 2923
  • Times Cited: 7419
  • 2) Mohamadi F.; Richards N.G.J; Guida W.C.; Still, W.C., Macromodel -an Intergrated
  • Software System for Modeling Organic and bioorganic Molecules Using Molecular
  • Mechanics, J. Comp. Chem., 1990, 11(4), 440
  • Times Cited: 2788
  • 3) Still, W.C.; Tempczyka, A.; Hawley R.C. Semianalytical Treatment of Solvation for
  • Molecular Mechanics and Dynamics, JACS, 1991, 112(16), 6127
  • Times Cited: 1511
  • Retired at 53 years old – Emeritus professor at Columbia University
  • Never got an NIH grant
  • Now building planes as a hobby.....
slide46

Prof. Louis Barriault

Graduate students

Jason Poulin

Minaruzaman

KassandraLepack

Francis Barabé

ChristianeGrisé-Bard

Eric Beaulieu (Past)

Marie-Christine Brochu (Past)

Steve Arns (Past)

Undergrads

Anne-Catherine Bédard

GrabrielBellavance

Jean-Francois Vincent-Rocan

Olivier Gagné

Patrick Lévesque (Past)

monensine
Monensine
  • 17 asymmmetric centers, 26 carbon backbone
  • theoretically 131 072 stereoisomers can exist
  • Polyether antibiotics constitute a growing class of naturally occurring ionophores.

Collum, D.B.; McDonald, J.H. III; Still, W. C., JACS, 1980, 102(2), 2117

retrosynthetic pathway
Retrosynthetic Pathway

Collum, D.B.; McDonald, J.H. III; Still, W. C., JACS, 1980, 102(2), 2117

monensin chromic acid degradation
Monensin- Chromic Acid Degradation
  • Why degradation ? :
    • Called relay synthesis
    • Structure proof of advanced synthetic intermediates
      • Ex: Stereochemistry

Dongwei, C.;Still, W.C.; J.Org. Chem., 1988, 53, 4641

monensin further degradation
Monensin – Further Degradation

Collum, D.B.; McDonald, J.H. III; Still, W. C., JACS, 1980, 102(2), 2117

monensin retrosynthetic scheme
Monensin- Retrosynthetic Scheme

Collum, D.B.; McDonald, J.H. III; Still, W. C., JACS, 1980, 102(2), 2117

monensin further degradation1
Monensin- Further Degradation

Collum, D.B.; McDonald, J.H. III; Still, W. C., JACS, 1980, 102(2), 2117

monensin further degradation2
Monensin- Further Degradation

Collum, D.B.; McDonald, J.H. III; Still, W. C., JACS, 1980, 102(2), 2117

monensin retrosynthetic scheme1
Monensin- Retrosynthetic Scheme

Collum, D.B.; McDonald, J.H. III; Still, W. C., JACS, 1980, 102(2), 2117

forward synthesis
Forward Synthesis

Collum, D.B.; McDonald, J.H.III;

Still, W.C., JACS, 1980, 102(6), 2118

forward synthesis1
Forward Synthesis

Collum, D.B.; McDonald, J.H.III; Still, W.C., JACS, 1980, 102(6), 2118

forward synthesis2
Forward Synthesis

Collum, D.B.; McDonald, J.H.III; Still, W.C., JACS, 1980, 102(6), 2118

forward synthesis3
Forward Synthesis

Collum, D.B.; McDonald, J.H.III; Still, W.C., JACS, 1980, 102(6), 2120

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