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Fluorous
Technologies, Inc. (FTI) is a chemical technology company dedicated
to the development and commercialization of fluorous products focused
at the life science market. The company uses patented technology to
solve synthesis and separation problems spanning the entire drug discovery
and development process. FTI further leverages its enabling technology
through service contracts, licenses, and collaborations.
Fluorous Technologies Releases Thirteen New Products
The FTI research and development team continues to synthesize innovative
products to fit your chemistry needs. Check out our product
development page with thirteen new products. If you have a product
need that is not in our catalog, please email
us to find out if we can make it for you. We'd also be happy to
hear about your new product ideas or planned fluorous publications.
Fluorous Mixture Synthesis (FMS) of Murisoline Diastereomers
In a recent article published in J. Am. Chem. Soc. (ASAP article),
Prof. D. Curran and coworkers Q. Zhang, H. Lu, and C. Richard at the
University of Pittsburgh reported the synthesis of (+)-murisoline and
its diastereomers by FMS.
The murisoline family of acetogenins has 6 diastereocenters and this
research focused on the rapid synthesis of 16 stereoisomers of the dihydroxy
tetrahydrofuran fragment (shown at right) with the 4(R) and 34(S) centers
fixed.
 The fluorous mixture synthesis
approach started with M-1, a mixture of four enantiomerically
pure compounds, each tagged with a PMB group of differing fluorine content.
This mixture was then taken through multiple synthetic steps, including
2 splitting and parallel syntheses to provide M-2, which contains
4 mixtures of four tagged products (16 products in total). Fluorous
HPLC demixing of the 4 mixtures based on tag fluorine content followed
by detagging provided all 16 of the desired diastereomers of murisoline.
Since this fluorous mixture synthesis has a total of 39 steps, compared
to 156 steps that would be required to accomplish the same transformations
using traditional, non-mixture techniques, the efficiency advantage
is obvious. In previous studies conducted by Prof. Curran and FTI, fluorous
mixture synthesis has been used to make two enantiomers of pyridovericin
(J.
Am. Chem. Soc. 2002,
124, 5774) and 560 analogs of mappicine (J.
Am. Chem. Soc. 2002,
124, 10443; Science
2001,
291, 1766).
FTI's End of Year Promotional Offer
As the year draws to an end, and many of your budgets face expiration,
we would like to offer you an incentive to use Fluorous Technologies'
reagents and sorbents in your research. Because we are certain that
FluoroFlash® products will have a positive impact on your
research, we are currently offering to new customers $100
off your first purchase or 30% off
your first purchase over $1000. This offer will be valid through December
19, 2003. Please see our ordering
information page for how to place an order.
Please take a look at www.fluorous.com
for our online catalog or download our PDF
catalog. Both contain application notes for many of our reagents
and sorbents and references to many of our publications. While you are
on the website, please take a moment to complete our short registration
survey so that we can continue to deliver information catered to your
needs in a timely manner.
FTI's Product Selection Chart for Amine and Amide Chemistry
In an effort to make your fluorous product selection easier, FTI has
released a product
selection tool for Amine and Amide chemistry. If you have specific
product questions, please contact Kris Mikulan, our technical support
specialist by clicking here.
Cutting Edge Fluorous Chemistry
Fluorous Chemistry in Solid-Phase Peptide Synthesis:
Recently, Overkleeft et al at Leiden University reported
the use of a fluorous Msc (F-Msc) tag in the synthesis and purification
of peptides produced by traditional solid-phase techniques.[1]
The F-Msc group was found to be a base labile protecting group ideally
suited for use in standard Fmoc-based peptide synthesis with Boc
or t-Bu side chain protection using Wang or Rink amide resins.
Amino acid couplings were carried out using HCTU or BOP/HOBt with
any deletion sequences acetyl capped after each coupling. After
the final Fmoc deprotection the peptide was tagged with F-Msc-Cl
rendering the desired peptide fluorous and all deletion sequences
non-fluorous. Resin cleavage and side chain deprotection were conducted
under acidic conditions. The tagged sequence was then easily purified
using either fluorous HPLC or fluorous solid extraction (F-SPE)
using FluoroFlash®
cartridges. Detagging with 2% aq. NH3 provided the
final peptide in high purity. For example, peptides containing
16-35 amino acids were produced using this strategy with purities
of 94-98% using fluorous HPLC and up to 91% using F-SPE. If you
are interested in purchasing this novel protecting group and its
applicability to peptide synthesis, please drop
us a line.
Fluorous
Technologies, Inc. (FTI) is a chemical technology company dedicated
to the development and commercialization of fluorous products focused
at the life science market. The company uses patented technology to
solve synthesis and separation problems spanning the entire drug discovery
and development process. FTI further leverages its enabling technology
through service contracts, licenses, and collaborations.
For further information please contact FTI
at 412-826-3050. We value your privacy. To learn more about how FTI uses
personal information, consult our privacy policy. To
unsubscribe from this newsletter, please reply to this email with
"unsubscribe" in the subject line.
FluoroFlash® is a registered trademark of Fluorous
Technologies, Inc.
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Contents
Fluorous
Technologies Releases Thirteen New Products
Fluorous
Mixture Synthesis (FMS) of Murisoline Diastereomers
FTI's
End of Year Promotional Offer
FTI's
Product Selection Chart for Amine and Amide Chemistry
Cutting
Edge Fluorous Chemistry
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