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{{chembox {{Chembox
| verifiedrevid = 400128403 | verifiedrevid = 400128403
|ImageFile=Lactacystin.svg | ImageFile = Lactacystin.svg
| ImageFile_Ref = {{chemboximage|correct|??}}
|ImageSize= | ImageSize = 244
⚫ |IUPACName=(2''R'')-2-(acetylamino)-3--4-methyl-5-oxopyrrolidin-2-yl}<br>carbonyl)sulfanyl]propanoic acid
| ImageName = Stereo skeletal formula of lactacystin
|OtherNames=
⚫ | IUPACName = 2-(acetylamino)-3--4-methyl-5-oxopyrrolidin-2-yl}carbonyl)sulfanyl]propanoic acid
|Section1= {{Chembox Identifiers | Section1 = {{Chembox Identifiers
⚫ | InChI = 1/C15H24N2O7S/c1-6(2)10(19)15(11(20)7(3)12(21)17-15)14(24)25-5-9(13(22)23)16-8(4)18/h6-7,9-11,19-20H,5H2,1-4H3,(H,16,18)(H,17,21)(H,22,23)/t7-,9+,10-,11+,15-/m1/s1
⚫ | CASNo = 133343-34-7
⚫ | InChIKey = DAQAKHDKYAWHCG-WBMULXAQBF
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} | CASNo_Ref = {{cascite|correct|??}}
⚫ | PubChem = 3870
⚫ | StdInChI = 1S/C15H24N2O7S/c1-6(2)10(19)15(11(20)7(3)12(21)17-15)14(24)25-5-9(13(22)23)16-8(4)18/h6-7,9-11,19-20H,5H2,1-4H3,(H,16,18)(H,17,21)(H,22,23)/t7-,9+,10-,11+,15-/m1/s1
| PubChem_Ref = {{Pubchemcite|changed|PubChem}}
⚫ | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| PubChem1 =
⚫ | StdInChIKey = DAQAKHDKYAWHCG-WBMULXAQSA-N
| PubChem1_Ref = {{Pubchemcite|correct|PubChem}}
⚫ | SMILES1 = O1(C)C(=O)N1(C(=O)SC(NC(C)=O)C(O)=O)(O)(C)C
| PubChem1_Comment = <small>-2-((1''S'')-1-hydrox)prop</small>
⚫ | CASNo=133343-34-7
| PubChem2 = 45039639
⚫ | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| PubChem2_Ref = {{Pubchemcite|correct|PubChem}}
⚫ | ChemSpiderID=21106450
| PubChem2_Comment = <small>(3''S'',4''R'')-3-hydrox,-2-((1''R'')-1-hydrox)prop,-4-meth</small>
⚫ | PubChem=6610292
| PubChem3 = 46782036
⚫ | SMILES = O1(C)C(=O)N1(C(=O)SC(NC(C)=O)C(O)=O)(O)(C)C
| PubChem3_Ref = {{Pubchemcite|correct|PubChem}}
⚫ | SMILES=CC(=O)N(CSC(=O)1((O)C(C)C)NC(=O)(C)1O)C(=O)O
| PubChem3_Comment = <small>(2''R'')-2-amid, (3''S'',4''R'')-3-hydrox,-2-((1''R'')-1-hydrox)prop,-4-meth</small>
⚫ }}
| PubChem4 = 3034764
⚫ |Section2= {{Chembox Properties
| PubChem4_Ref = {{Pubchemcite|correct|PubChem}}
| C=15|H=24|N=2|O=7|S=1
| PubChem4_Comment = <small>(2''R'')-2-amid, (3''S'',4''R'')-3-hydrox,-2-((1''S'')-1-hydrox)prop,-4-meth</small>
| MolarMass=
⚫ | ChemSpiderID = 3735
| Appearance=
⚫ | ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
| Density=
| ChemSpiderID1 = 2299173
| MeltingPt=
| ChemSpiderID1_Ref = {{chemspidercite|correct|chemspider}}
| BoilingPt=
| ChemSpiderID1_Comment = <small>(2''R'')-2-amid, (3''S'',4''R'')-3-hydrox,-2-((1''S'')-1-hydrox)prop,-4-meth</small>
| Solubility=
| MeSHName = Lactacystin
⚫ }}
| ChEBI = 52722
|Section3= {{Chembox Hazards
| ChEMBL = 374308
| MainHazards=
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| FlashPt=
⚫ | SMILES = CC(C)C(O)C1(NC(=O)C(C)C1O)C(=O)SCC(NC(C)=O)C(O)=O
| Autoignition=
⚫ | SMILES1 = CC(=O)NC(CSC(=O)C1(C(O)C(C)C)NC(=O)C(C)C1O)C(=O)O
}}
⚫ | SMILES2 = OC1C(C)C(=O)NC1(C(=O)SCC(NC(C)=O)C(O)=O)C(O)C(C)C
⚫ | StdInChI = 1S/C15H24N2O7S/c1-6(2)10(19)15(11(20)7(3)12(21)17-15)14(24)25-5-9(13(22)23)16-8(4)18/h6-7,9-11,19-20H,5H2,1-4H3,(H,16,18)(H,17,21)(H,22,23)
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
⚫ | InChI = 1/C15H24N2O7S/c1-6(2)10(19)15(11(20)7(3)12(21)17-15)14(24)25-5-9(13(22)23)16-8(4)18/h6-7,9-11,19-20H,5H2,1-4H3,(H,16,18)(H,17,21)(H,22,23)
⚫ | StdInChIKey = DAQAKHDKYAWHCG-UHFFFAOYSA-N
⚫ | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
⚫ | InChIKey = DAQAKHDKYAWHCG-WBMULXAQBF
}} }}
⚫ | Section2 = {{Chembox Properties
| C = 15
| H = 24
| N = 2
| O = 7
| S = 1
| ExactMass = 376.130421822 g mol<sup>-1</sup>
| LogP = 0.086
| pKa = 3.106
| pKb = 10.891
⚫ }}
⚫ }}

'''Lactacystin''' is an ] naturally ] by ] of the ] '']'' first described in 1991.<ref name="Omura">Omura S, Fujimoto T, Otoguro K, Matsuzaki K, Moriguchi R, Tanaka H, Sasaki Y. (1991). Lactacystin, a novel microbial metabolite, induces neuritogenesis of neuroblastoma cells: S. Omura, et al. ''J. Antibiot.'' 44(1):113-6.</ref> The first ] of lactacystin was developed by ] in 1992.<ref name="Corey">''"Total Synthesis of Lactacystin"'' Corey, E. J.; Reichard, G. A. '']'' '''1992''', ''114'', 10677.</ref> The molecule is most commonly used as in ] and ] laboratories as a selective inhibitor of the ].<ref name="Fenteany">Fenteany G, Standaert RF, Lane WS, Choi S, Corey EJ, Schreiber SL. (1995) Inhibition of proteasome activities and subunit-specific amino-terminal threonine modification by lactacystin. ''Science'' 268:726-731.</ref><ref name="Orlowski">Orlowski RZ. (1999). The role of the ubiquitin-proteasome pathway in apoptosis. ''Cell Death Differ'' 6: 303-313.</ref> The molecule is a ], or cyclic ]. A number of syntheses of this molecule have been published and there are no less than 1,300 references to this natural product in the literature.<ref name="Brennan">Christopher J. Brennan, Gerald Pattenden, Gwenaella Rescourio . (2003). Formal Synthesis of (+)-Lactacystin Based on a Novel Radical Cyclization of an -Ethynyl-Substituted Serine: C Brennan et al. ''Tetrahedron Lett'' 44 (2003) 49, 8757-8760.</ref> '''Lactacystin''' is an ] naturally ] by ] of the ] '']'' first described in 1991.<ref name="Omura">Omura S, Fujimoto T, Otoguro K, Matsuzaki K, Moriguchi R, Tanaka H, Sasaki Y. (1991). Lactacystin, a novel microbial metabolite, induces neuritogenesis of neuroblastoma cells: S. Omura, et al. ''J. Antibiot.'' 44(1):113-6.</ref> The first ] of lactacystin was developed by ] in 1992.<ref name="Corey">''"Total Synthesis of Lactacystin"'' Corey, E. J.; Reichard, G. A. '']'' '''1992''', ''114'', 10677.</ref> The molecule is most commonly used as in ] and ] laboratories as a selective inhibitor of the ].<ref name="Fenteany">Fenteany G, Standaert RF, Lane WS, Choi S, Corey EJ, Schreiber SL. (1995) Inhibition of proteasome activities and subunit-specific amino-terminal threonine modification by lactacystin. ''Science'' 268:726-731.</ref><ref name="Orlowski">Orlowski RZ. (1999). The role of the ubiquitin-proteasome pathway in apoptosis. ''Cell Death Differ'' 6: 303-313.</ref> The molecule is a ], or cyclic ]. A number of syntheses of this molecule have been published and there are no less than 1,300 references to this natural product in the literature.<ref name="Brennan">Christopher J. Brennan, Gerald Pattenden, Gwenaella Rescourio . (2003). Formal Synthesis of (+)-Lactacystin Based on a Novel Radical Cyclization of an -Ethynyl-Substituted Serine: C Brennan et al. ''Tetrahedron Lett'' 44 (2003) 49, 8757-8760.</ref>


==References== ==References==
{{Reflist}}
<references />


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Revision as of 03:49, 4 February 2011

Lactacystin
Stereo skeletal formula of lactacystin
Names
IUPAC name 2-(acetylamino)-3--4-methyl-5-oxopyrrolidin-2-yl}carbonyl)sulfanyl]propanoic acid
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
  • 3735
  • 2299173 (2R)-2-amid, (3S,4R)-3-hydrox,-2-((1S)-1-hydrox)prop,-4-meth
MeSH Lactacystin
PubChem CID
  • 3870
  • 45039639 (3S,4R)-3-hydrox,-2-((1R)-1-hydrox)prop,-4-meth
  • 46782036 (2R)-2-amid, (3S,4R)-3-hydrox,-2-((1R)-1-hydrox)prop,-4-meth
  • 3034764 (2R)-2-amid, (3S,4R)-3-hydrox,-2-((1S)-1-hydrox)prop,-4-meth
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C15H24N2O7S/c1-6(2)10(19)15(11(20)7(3)12(21)17-15)14(24)25-5-9(13(22)23)16-8(4)18/h6-7,9-11,19-20H,5H2,1-4H3,(H,16,18)(H,17,21)(H,22,23)Key: DAQAKHDKYAWHCG-UHFFFAOYSA-N
  • InChI=1/C15H24N2O7S/c1-6(2)10(19)15(11(20)7(3)12(21)17-15)14(24)25-5-9(13(22)23)16-8(4)18/h6-7,9-11,19-20H,5H2,1-4H3,(H,16,18)(H,17,21)(H,22,23)Key: DAQAKHDKYAWHCG-WBMULXAQBF
SMILES
  • CC(C)C(O)C1(NC(=O)C(C)C1O)C(=O)SCC(NC(C)=O)C(O)=O
  • CC(=O)NC(CSC(=O)C1(C(O)C(C)C)NC(=O)C(C)C1O)C(=O)O
  • OC1C(C)C(=O)NC1(C(=O)SCC(NC(C)=O)C(O)=O)C(O)C(C)C
Properties
Chemical formula C15H24N2O7S
Molar mass 376.42 g·mol
log P 0.086
Acidity (pKa) 3.106
Basicity (pKb) 10.891
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). checkY verify (what is  ?) Infobox references
Chemical compound

Lactacystin is an organic compound naturally synthesized by bacteria of the genus Streptomyces first described in 1991. The first total synthesis of lactacystin was developed by Elias Corey in 1992. The molecule is most commonly used as in biochemistry and cell biology laboratories as a selective inhibitor of the proteasome. The molecule is a lactam, or cyclic amide. A number of syntheses of this molecule have been published and there are no less than 1,300 references to this natural product in the literature.

References

  1. Omura S, Fujimoto T, Otoguro K, Matsuzaki K, Moriguchi R, Tanaka H, Sasaki Y. (1991). Lactacystin, a novel microbial metabolite, induces neuritogenesis of neuroblastoma cells: S. Omura, et al. J. Antibiot. 44(1):113-6.
  2. "Total Synthesis of Lactacystin" Corey, E. J.; Reichard, G. A. J. Am. Chem. Soc. 1992, 114, 10677.
  3. Fenteany G, Standaert RF, Lane WS, Choi S, Corey EJ, Schreiber SL. (1995) Inhibition of proteasome activities and subunit-specific amino-terminal threonine modification by lactacystin. Science 268:726-731.
  4. Orlowski RZ. (1999). The role of the ubiquitin-proteasome pathway in apoptosis. Cell Death Differ 6: 303-313.
  5. Christopher J. Brennan, Gerald Pattenden, Gwenaella Rescourio . (2003). Formal Synthesis of (+)-Lactacystin Based on a Novel Radical Cyclization of an -Ethynyl-Substituted Serine: C Brennan et al. Tetrahedron Lett 44 (2003) 49, 8757-8760.
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