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Natural Science Forum / Chemistry / Organic Synthesis / July 2003



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JB - 14 Jul 2003 17:43 GMT
Sorry I don't know if I should be posting this in a technical forum...

Anyway, I need to make a solution using a proteasome inhibitor
(Carbobenzoxy-L-isoleucyl-(gamma)-t-butyl-L-glutamyl-L-alanyl-L-leucinal.
Z-Ile-Glu(OBut)-Ala-Leu-H (aldehyde).)It's a Cell-permeable inhibitor
of the multicatalytic proteinase complex Proteasome in HT4 cells.

I want to create a vehicle using Propylene Glycol 50%, Deionized Water
20%, and Ethanol 30%. However, because the PSI compound has been
lyophilized as an amorphous powder from DMSO solution I'm worried that
my vehicle may cause the compound to racemize. The undissolved peptide
is stable below -20C. Once prepared with the vehicle would it be
stable at room temp?

Anyone know?
Signature

Paul J. Franklin(moderator - sci.chem.organic.synthesis)
http://organicworldwide.net/sci.chem.organic.synthesis
Georgia State University <chepjf@panther.gsu.edu>
Atlanta, GA

Uncle Al - 15 Jul 2003 16:46 GMT
> Sorry I don't know if I should be posting this in a technical forum...

> Anyway, I need to make a solution using a proteasome inhibitor
> (Carbobenzoxy-L-isoleucyl-(gamma)-t-butyl-L-glutamyl-L-alanyl-L-leucinal.
> Z-Ile-Glu(OBut)-Ala-Leu-H (aldehyde).)It's a Cell-permeable inhibitor
> of the multicatalytic proteinase complex Proteasome in HT4 cells.

> I want to create a vehicle using Propylene Glycol 50%, Deionized Water
> 20%, and Ethanol 30%. However, because the PSI compound has been
> lyophilized as an amorphous powder from DMSO solution I'm worried that
> my vehicle may cause the compound to racemize. The undissolved peptide
> is stable below -20C. Once prepared with the vehicle would it be
> stable at room temp?

Lyophilized from DMSO?  Either somebody was very good indeed or
somebody is lying.  How much DMSO is still in the powder?  What is the
optical rotation of the peptide?  See if you can jury rig an optical
rotation measurement from a solution-filled melting point capillary.
Either have microscope cover slips for Super Glued windows, or glue in
an optical fiber on each end to seal the filled capillary.  Get the
real world answer.

(Not so hard:  Monochromatic LED light (disassembled laser pointer,
pick your color) in through an optical fiber, past a linear polarizer
(careful here if it is a laser diode source), through the cap, past a
second rotated polarizer to give minimal tranmission, then to a
snugged photodiode and a meter.  If the stuff racemizes the
transmission increases.  Control the temp.  Take an occasional reading
over time.  Continuous is bad.  Why?)

Signature

Uncle Al
http://www.mazepath.com/uncleal/
(Toxic URL! Unsafe for children and most mammals)
"Quis custodiet ipsos custodes?"  The Net!
--
Paul J. Franklin(moderator - sci.chem.organic.synthesis)
http://organicworldwide.net/sci.chem.organic.synthesis
Georgia State University <chepjf@panther.gsu.edu>
Atlanta, GA

Steve Turner - 17 Jul 2003 16:01 GMT
Uncle Al <UncleAl0@hate.spam.net> wrote:

>Lyophilized from DMSO?  Either somebody was very good indeed or
>somebody is lying.

Strange but true - DMSO can be removed by lyophilization.  I didn't
believe it at first either.

Steve Turner

Real address contains worldnet instead of spamnet
Signature

Paul J. Franklin(moderator - sci.chem.organic.synthesis)
http://organicworldwide.net/sci.chem.organic.synthesis
Georgia State University <chepjf@panther.gsu.edu>
Atlanta, GA

 
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