Cem's Microwave Peptide Synthesizer Allows ... - CEM Gmbh

REFERENCES
Microwave Heating for Solid-Phase Peptide Synthesis: General Evaluation and Application
to 15-mer Phosphopeptides, Brandt M., Gammeltoft S., Jensen, K.J., International Journal of
Peptide Research and Therapeutics (In Press)
Rapid solid-phase peptide synthesis using thermal and controlled microwave irradiation, Bernadett
Bacsa, Bimbisar Desai, Gabor Dibo, C. Oliver Kappe, J. Pept. Sci. (In Press)
Solid Phase Peptide Synthesis under Microwave, J.M. Collins, M.J. Collins, Chapter 20 in
Microwaves in Organic Synthesis, Wiley-VCH, Weinheim 2006.
Fast and versatile microwave-assisted intramolecular heck reaction in peptide macrocyclization
using microwave energy, Gerardo Byk, Mirit Cohen-Ohana, Daniel Raichman, Biopolymers 84,
274-282 2006.
Rapid and effi cient synthesis of the pentapeptide of elastin protein and peptides containing
highly hindered a,a-dialkyl amino acids employing Fmoc-amino acid chlorides under microwave
irradiation in the solution phase, Subramanyam J. Tantry, R.V. Ramana Rao, V.V. Suresh
Babu, ARKIVOC 2006 (I) 21-30.
Construction of Highly Glycosylated Mucin-Type Glycopeptides Based on Microwave-Assisted
Solid-Phase Synthesis and Enzymatic Modifi cations, Takahiko Matsushita, Hiroshi Hinou,
Masataka Fumoto, Masaki Kurogochi, Naoki Fujitani, Hiroki Shimizu, Shin-Ichiro Nishimura,
J. Org. Chem., 71, 3051-3063, 2006.
Microwave-assisted coupling with DIC/HOBt for the synthesis of diffi cult peptoids and fl uorescently
labelled peptides-a gentle heat goes a long way, Mario A. Fara, Juan Jose Diaz-Mochon,
Mark Bradley, Tetrahedron Lett. 47, 1011-1014, 2006.
Effects of i and i+3 Residue Identity on Cis-Trans Isomerism of the Aromatici+1-Prolyli+2
Amide Bond: Implications for Type VI b-turn Formation, Meng H.Y., Thomas K.M., Lee A.E.,
Zondlo N.J., Peptide Science 84, 192-204, 2005.
Expedient synthesis and design strategies for new peptoid construction, Gorske BC, Jewell SA.,
Guerard EJ, Blackwell HE, Org. Lett., 7, 1521-1524, 2005.
Rapid Microwave-Assisted Solid-Phase Glycopeptide Synthesis, Takahiko Matsushita, Hiroshi
Hinou, Masaki Kurogochi, Hiroki Shimizu, Shin-Ichiro Nishimura, Org. Lett., 7, 5, 2005.
Solid-Phase Synthesis of Conformationally Contstrained Peptidomimetics Based on a 3,6-Disubstituted-1,4-diazepan-2,5-dione
Core, Lucia Raffaella Lampariello, Daniela Piras, Manuela
Rodriquez, Maurizio Taddei, J. Org. Chem. Note, 2003.
Introduction of 4(S)-oxazolidineacetic acid, 2-oxo (D-Oxac) motif in a polypeptide chain:
synthesis and conformational analysis, Gianluigi Luppi, Marzia Villa, Claudia Tomasini, Org.
Biomol. Chem., 1, 247-250, 2003.
Microwave-Assisted Solid Phase Synthesis of Peptoids, Hernando J. Olivos, Prasanna G. Alluri,
M. Muralidhar Reddy, Derek Salony, Thomas Kodadek, Org. Lett., 4, 23 2002.
Rapid Microwave-Assisted Solid Phase Peptide Synthesis, Mate Erdelyi, Adolf Gogoll, Synthesis,
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CEM’s Microwave Peptide Synthesizer Allows Mimotopes to
Successfully Synthesize Diffi cult 52mer Peptide
Synthesis Not Previously Possible Under Conventional Conditions
Australian biotechnology company Mimotopes, a wholly owned subsidiary of PharmAust (ASX:PAA) and Phylogica
(ASX:PYC), has successfully utilized the CEM Liberty Microwave Peptide Synthesizer to synthesize a long, diffi
cult peptide sequence known as Phylomers®. Using the Liberty, Mimotopes was able to obtain a crude purity of ~
65% with a total synthesis time of 48 hours. Previous attempts using conventional technology yielded < 5% crude
purity with a signifi cantly longer synthesis time.
Phylomers®
Sequence: GRKKRRQRRRGKDSIRRRGENISSQEVEAVLMSHPEVVNAAVYPVRGDLPGD
LC/MS Trace at 214nm of the crude peptide product of Phylomers® from the Liberty
In August 2005, Phylogica signed a partnering deal with Melbourne-based Mimotopes Pty Ltd, a global leader in the
development of pre-clinical peptides for biological and pharmaceutical applications. Mimotopes’ proprietary technologies
in peptide synthesis provide it with a unique ability to produce large libraries of long and unusual peptides,
including Phylomer® peptides. Using their complementary technology platforms, Phylogica and Mimotopes are now
working together to develop the next generation of peptide drugs.
CEM
Corporation
Applied
Biosystems
Protein Technologies
System Liberty ABI433A Symphony® Prelude
Microwave
Yes- Single mode,
self-tuning
None None None
Cycle Time 25 minutes 1-2 hours 1-2 hours 1-2 hours
Scale 0.025 – 5.0mmol 0.1 – 1.0mmol 0.005 – 0.35mmol 0.01 – 2.0mmol
Washing
(Spray Head)
Amino Acid
Reservoirs
Yes No No Yes
25 reservoirs up
to 250mL each
Conventional
9.6% Purity
37.2% Crude Yield
Couplings
completed in
10 min vs
180 min*
Cleavage in
30 min vs
12-15 hours*
*Org. Lett,
2001, 3, 1201.
50 – single shot
vials(any double
couplings used on a
particular amino acid
will take 2 cartridges)
20 reservoirs up to
100mL each(no extra
reservoirs for unusual
amino acids)
27 reservoirs up
to 100mL each
Advantage
CEM’s patented Liberty System is the ONLY
System to feature a microwave cavity to
enhance solid phase peptide synthesis.
deprotection and 5-minute coupling reaction
time standard. This allows for the industry’s
fastest complete cycle times of 25-minutes.
CEM offers the widest scale range available.
While other manufacturers claim a lower
small scale, this is a game of diluting reagents
and not important unless utilizing a parallel
96-well type system.
The ability to add solvent to the reaction
vessel from the top and bottom for washing
ensures the least possible carryover. It also
ensures that resin stuck to the side of the
walls is pushed back into the solution.
Liberty’s reservoir capacity allows greater
fl exibility and routine use of unusual reagents.
1-42 ß-amyloid
DA - EFRHDSGYEV - HHQKLVFFAE - DVGSNKGAII - GLMVGGVVIA
Total Microwave Synthesis time of 19 hours
Microwave
68.8% Purity
40% Crude Yield
Synthesize Polyamides in Hours, not days... with 90% Purity.
Peptide = Ac-Im-Im-Py-Py-gamma-
Im-Py-Py-Py-beta-Dp
Mw=1280.36