User:Etienne Robillard/Notebook/Schiff base

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=== Introduction to Schiff bases ===
=== Introduction to Schiff bases ===
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* Insert text here in scientifically acceptable way (ie: without grammar errors) to explain the functions and basics of [http://chemwiki.ucdavis.edu/Organic_Chemistry/Organic_Chemistry_With_a_Biological_Emphasis/Chapter_11:_Nucleophilic_carbonyl_addition_reactions/Section_11.6:_Imine_(Schiff_base)_formation Schiff base formation]. [1]  
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Learning resources:
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* Part 1: [http://chemwiki.ucdavis.edu/Organic_Chemistry/Organic_Chemistry_With_a_Biological_Emphasis/Chapter_11:_Nucleophilic_carbonyl_addition_reactions/Section_11.6:_Imine_(Schiff_base)_formation Schiff base formation]. [1]
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* Part 2: [http://www.chem.ucalgary.ca/courses/350/Carey5th/Ch21/ch21-4-3.html Micheal reaction]
=== Schiff bases conjugated pharmacological intermediates and N-substituted heterocyclics carbenes ===
=== Schiff bases conjugated pharmacological intermediates and N-substituted heterocyclics carbenes ===
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* Question 3 (bonus question) : In your own words, describe the role of a synthase enzyme (without the help of Wikipedia!) in the phosphorylation of ATP.
* Question 3 (bonus question) : In your own words, describe the role of a synthase enzyme (without the help of Wikipedia!) in the phosphorylation of ATP.
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=== Formation of phenylmethylamine as the tautomeric form of a ethyl-methyl carbanion ===
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=== Troika acids; Formation of phenylmethylamine as the tautomeric form of a ethyl-methyl Carbanion (Cyanide) ligands : 4-trans-7-aminoalkylamino-2,1,3-benzoxadiazoles, 1,2-dimethylcyclohexanes and friends :) ===
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* For the long story, see [[Phenylmethylamine]]: A nucleophilic Schiff base where the N-substituted anion is fused to a benzene ring (?) to yield a '''enamine'''. See also [[Ethanamine]]. Note that the C=N double bond is the result (product) of asymmetric synthesis (<font color="red">Micheal addition</font>) in presence of a organometal catalyst.  
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Student resources:
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* assert biological relevance of Parkinson disease [2] as the result of prolonged 1,2,3,4-tetrahydroisoquinolines derivatives absorption: A 2-phenylmethylamine-specific enatiomer ?
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* [[User:Etienne_Robillard/Notebook/Phenylmethanamine|Phenylmethanamine]]
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* [[Ethanamine]]
 +
 
 +
Teaching Topics:
 +
* Troika acids
 +
* Toxicity of cyanophosphate-derived cross-linker reagents exposure : Alcoholism like psychotic symptoms. Acute psychotic (visual..) hallucinations (Note: Long-term rehabilitation is often necessary.. :)
 +
* Effects of cyanide on Yb(OTf)3 conformational polypeptide (1,2,3,4-tetrahydroisoquinolines) isomerisation ?
 +
* Remote activation of <font color=purple>Gold</font> (Yb) nanoparticles ? hmm.. star trek style drug delivery :)
 +
 
 +
Notes:
 +
* <font color=purple style="background:#ddd">'''The [Ph]C=N double bond linkage may be a result (product) of asymmetric synthesis (<font color="red">Micheal addition</font>) in presence of a organometal catalyst. [1]</font> [[Image:500px-Diethyl cyanophosphate.svg.png|thumb|right|Example cyanophosphate-derived synthetic reagent. (PMID: 1818086, 15670935)]]
 +
* Assert biological relevance of Parkinson disease [2] as the result of prolonged 1,2,3,4-tetrahydroisoquinolines derivatives absorption: A 2-phenylmethylamine-specific enatiomer ?
* Additional data is provided in [http://brenda-enzymes.org/php/result_flat.php4?ecno=2.1.1.28&Suchword=&organism%5B%5D=Homo+sapiens&show_tm=0 EC 2.1.1.28] to confirm a solid link between Parkinson disease and novel tetrahydroisoquinolines derivatives. -- Check this. -[[User:Etienne_Robillard|ER]]
* Additional data is provided in [http://brenda-enzymes.org/php/result_flat.php4?ecno=2.1.1.28&Suchword=&organism%5B%5D=Homo+sapiens&show_tm=0 EC 2.1.1.28] to confirm a solid link between Parkinson disease and novel tetrahydroisoquinolines derivatives. -- Check this. -[[User:Etienne_Robillard|ER]]
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* tristable PD riboswitch abstrachachachatization: Check/verify the tri-stable RNA polymerase repressor functions (LuxR) and AHL evidences in the design of <font color="red">Schiff base conjugated C6 (hexanoyl) psychochemicals to induce (lazy) light-activated mRNA transcription and metabolism</font>. -[[User:Etienne_Robillard|ER]]  
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* tristable PD riboswitch abstrachachachatization: Check/verify the tri-stable mRNA polymerase repressor functions (LuxR) and AHL evidences in the design of <font color="red">Schiff base conjugated (6xHis tag) psychochemicals to induce (lazy) light-activated mRNA transcription and metabolism</font>. -[[User:Etienne_Robillard|ER]]  
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* Verify this lazy RNA polymerase function: 2ATP+CO2->Ph2CO<=>2(N+2(R)+OH) -[[User:Etienne_Robillard|ER]]
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* Also Verify this lazy RNA polymerase function: <math>2ATP+CO^2->Ph^2CO<=>2N+2ROH</math> -[[User:Etienne_Robillard|ER]]
* carbanion = cyanide anion
* carbanion = cyanide anion
 +
* 6his-tag = a C6 hexanoyl based heterocyclic carbanion -- N-substituted oxazoles derivatives (imine)
 +
 +
=== The Monsanto connection: Troika acids; novel cyanophosphonate compounds as N-substituted (alkyl) drug carrier (pharmacochemical intermediates) ===
 +
* US6218563 (cyanophosphonamides as recombinant polyhistidine tag)
 +
* US5935542 (cyanophosphonate derivatives compounds as a n-substituted Schiff base) (ie: <font color=purple>for binding ca2+/mg2+ ions to a recombinant "fusion" protein...</font>)
 +
* Chuck: If you want to spray civilians without impunity, be sure to include a cyanoethyl moeity...
 +
* Oracle: Are you kidding? Once upon a time cyanide was at the basis of the Zyklon-b pellet...
 +
* Oracle: Hence, the magnitude and scale of civilians exposure to the new compound is probably most effective today.
 +
* Chuck: For next time, how about a ban of spraying civilians with pharmacochemical intermediates ?
 +
* Oracle: Go ask Obama!
 +
* Chuck: LOL
 +
* Oracle: Go ask Monsanto! When should it become natural to breath air ? Is this a luxury reserved for an elite golf club ?
 +
* Chuck: And Is this the reason I'm being emprisonned ?
 +
* Chuck: Because I refuse to happily breath such things while the majority of the breed have no clue what the heck a troika acid is composed of?
=== References ===
=== References ===
-
# http://chemwiki.ucdavis.edu/Organic_Chemistry/Organic_Chemistry_With_a_Biological_Emphasis/Chapter_11:_Nucleophilic_carbonyl_addition_reactions/Section_11.6:_Imine_(Schiff_base)_formation
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# [http://chemwiki.ucdavis.edu/Organic_Chemistry/Organic_Chemistry_With_a_Biological_Emphasis/Chapter_11:_Nucleophilic_carbonyl_addition_reactions/Section_11.6:_Imine_(Schiff_base)_formation Imine (Schiff base) formation] - Highly recommended primer documentation on Schiff bases
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# http://www.wikigenes.org/e/chem/e/7046.html
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# http://www.wikigenes.org/e/chem/e/7046.html - 1,2,3,4-tetrahydroisoquinoline. (Note: A anti-malarial pharmaceutical compound comparable to mefloquine. Compound may be implicated in 4-trans like enantiomer substitution (conformational) leading to '''acute psychotic hallucinations'''. See: [[User:Etienne_Robillard/Notebook/Arylcyclohexylamines|Arylcyclohexylamines]] and [http://chemistry.umeche.maine.edu/CHY251/cyclo6.html this document] for a more concise explanation.) 
 +
 
 +
<font color=purple style="background:#ddd">Synthesis and conformational rearrangement of benzoxadiazole derivatives with disubstituted (-N=Ph[2]C) isocyanate ligands [phosphoramido-cyanidate]</font>
 +
# DOI:10.1021/ja00132a045 [ISOCYANIDES1]
 +
# DOI:10.1002/anie.197205301 [ISOCYANIDES2] (<font color=purple style="background: #ddd">Hofmann/Ugi route to PS, Wilmslow</font>)
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# http://www.ncbi.nlm.nih.gov/pubmed/16953613
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# http://www.nizkor.org/ftp.cgi/camps/auschwitz/cyanide/cyanide.001
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# http://www.state.gov/www/global/arms/treaties/cwc/cwcann.html - In Schedule 1A(2), Schedule 2B(6)
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 +
Tyrosine kinase (GPCR) signaling with Troika acids (disubstituted Chair Conformer Cyclohexane Ring system):
 +
# ​[http://www.plantphysiol.org/content/148/3/1668 Protein Tyrosine Kinases and Protein Tyrosine Phosphatases Are Involved in Abscisic Acid-Dependent Processes in Arabidopsis Seeds and Suspension Cells]
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# [http://www.ncbi.nlm.nih.gov/pmc/articles/PMC156371/ Small Ubiquitin-Like Modifier Modulates Abscisic Acid Signaling in Arabidopsis]
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# cis/trans stuff (Look for section "Conformational Structures of Disubstituted Cyclohexanes", 4th row from the top) : http://www2.chemistry.msu.edu/faculty/reusch/VirtTxtJml/sterism2.htm
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 +
=== Did you know? ===
 +
 
 +
'"Attitude is a little thing that makes a big difference." - Winston Churchill

Revision as of 14:04, 18 May 2013

Contents

Introduction to Schiff bases

Learning resources:

Schiff bases conjugated pharmacological intermediates and N-substituted heterocyclics carbenes

  • Present summarly the basic psychopharmacological aspects/functions of imine in a biological system .
    • pharmacological intermediates (N-substituted heterocyclics)
    • Nucleophilic carbonyl addition
    • PS: Yb(OTf)3 route to 1,2,3,4-tetrahydroisoquinolines derivatives.
    • Micheal addition=>PS (Pictet-Spengler asymmetric synthesis of 1,2,3,4-tetrahydroisoquinolines)

Schiff bases as quorum sensing molecules (AHL) and Serine-dependent osmolitic regulators/ATP synthase

  • Question 1 : In your own words, explain at least 2 functions of the envZ/30C6HSL (ATP-dependent) synthetase in E. coli.
  • Question 2 : How is EnvZ relevant to CES (ADA) and specifically the CAMK2G gene?
  • Note: Further info on Phenylmethylamine substituted beta-amyloid ligands (APP) are here.
  • Question 3 (bonus question) : In your own words, describe the role of a synthase enzyme (without the help of Wikipedia!) in the phosphorylation of ATP.

Troika acids; Formation of phenylmethylamine as the tautomeric form of a ethyl-methyl Carbanion (Cyanide) ligands : 4-trans-7-aminoalkylamino-2,1,3-benzoxadiazoles, 1,2-dimethylcyclohexanes and friends :)

Student resources:

Teaching Topics:

  • Troika acids
  • Toxicity of cyanophosphate-derived cross-linker reagents exposure : Alcoholism like psychotic symptoms. Acute psychotic (visual..) hallucinations (Note: Long-term rehabilitation is often necessary.. :)
  • Effects of cyanide on Yb(OTf)3 conformational polypeptide (1,2,3,4-tetrahydroisoquinolines) isomerisation ?
  • Remote activation of Gold (Yb) nanoparticles ? hmm.. star trek style drug delivery :)

Notes:

  • The [Ph]C=N double bond linkage may be a result (product) of asymmetric synthesis (Micheal addition) in presence of a organometal catalyst. [1]
    Example cyanophosphate-derived synthetic reagent. (PMID: 1818086, 15670935)
    Example cyanophosphate-derived synthetic reagent. (PMID: 1818086, 15670935)
  • Assert biological relevance of Parkinson disease [2] as the result of prolonged 1,2,3,4-tetrahydroisoquinolines derivatives absorption: A 2-phenylmethylamine-specific enatiomer ?
  • Additional data is provided in EC 2.1.1.28 to confirm a solid link between Parkinson disease and novel tetrahydroisoquinolines derivatives. -- Check this. -ER
  • tristable PD riboswitch abstrachachachatization: Check/verify the tri-stable mRNA polymerase repressor functions (LuxR) and AHL evidences in the design of Schiff base conjugated (6xHis tag) psychochemicals to induce (lazy) light-activated mRNA transcription and metabolism. -ER
  • Also Verify this lazy RNA polymerase function: 2ATP + CO2 − > Ph2CO < = > 2N + 2ROH -ER
  • carbanion = cyanide anion
  • 6his-tag = a C6 hexanoyl based heterocyclic carbanion -- N-substituted oxazoles derivatives (imine)

The Monsanto connection: Troika acids; novel cyanophosphonate compounds as N-substituted (alkyl) drug carrier (pharmacochemical intermediates)

  • US6218563 (cyanophosphonamides as recombinant polyhistidine tag)
  • US5935542 (cyanophosphonate derivatives compounds as a n-substituted Schiff base) (ie: for binding ca2+/mg2+ ions to a recombinant "fusion" protein...)
  • Chuck: If you want to spray civilians without impunity, be sure to include a cyanoethyl moeity...
  • Oracle: Are you kidding? Once upon a time cyanide was at the basis of the Zyklon-b pellet...
  • Oracle: Hence, the magnitude and scale of civilians exposure to the new compound is probably most effective today.
  • Chuck: For next time, how about a ban of spraying civilians with pharmacochemical intermediates ?
  • Oracle: Go ask Obama!
  • Chuck: LOL
  • Oracle: Go ask Monsanto! When should it become natural to breath air ? Is this a luxury reserved for an elite golf club ?
  • Chuck: And Is this the reason I'm being emprisonned ?
  • Chuck: Because I refuse to happily breath such things while the majority of the breed have no clue what the heck a troika acid is composed of?

References

  1. Imine (Schiff base) formation - Highly recommended primer documentation on Schiff bases
  2. http://www.wikigenes.org/e/chem/e/7046.html - 1,2,3,4-tetrahydroisoquinoline. (Note: A anti-malarial pharmaceutical compound comparable to mefloquine. Compound may be implicated in 4-trans like enantiomer substitution (conformational) leading to acute psychotic hallucinations. See: Arylcyclohexylamines and this document for a more concise explanation.)

Synthesis and conformational rearrangement of benzoxadiazole derivatives with disubstituted (-N=Ph[2]C) isocyanate ligands [phosphoramido-cyanidate]

  1. DOI:10.1021/ja00132a045 [ISOCYANIDES1]
  2. DOI:10.1002/anie.197205301 [ISOCYANIDES2] (Hofmann/Ugi route to PS, Wilmslow)
  3. http://www.ncbi.nlm.nih.gov/pubmed/16953613
  4. http://www.nizkor.org/ftp.cgi/camps/auschwitz/cyanide/cyanide.001
  5. http://www.state.gov/www/global/arms/treaties/cwc/cwcann.html - In Schedule 1A(2), Schedule 2B(6)

Tyrosine kinase (GPCR) signaling with Troika acids (disubstituted Chair Conformer Cyclohexane Ring system):

  1. Protein Tyrosine Kinases and Protein Tyrosine Phosphatases Are Involved in Abscisic Acid-Dependent Processes in Arabidopsis Seeds and Suspension Cells
  2. Small Ubiquitin-Like Modifier Modulates Abscisic Acid Signaling in Arabidopsis
  3. cis/trans stuff (Look for section "Conformational Structures of Disubstituted Cyclohexanes", 4th row from the top) : http://www2.chemistry.msu.edu/faculty/reusch/VirtTxtJml/sterism2.htm

Did you know?

'"Attitude is a little thing that makes a big difference." - Winston Churchill

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