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Stable Isotope Labeled
Reagents from ISOTEC®
Stable isotope containing compounds are used in a variety of applications
including tracers in clinical studies, 1 labeled amino acids for use in
protein quantifi cation 2 and standards for metabolic research. 3 Historically,
the introduction of stable isotopes has been a diffi cult, time consuming
and costly process requiring the specialized skill of a stable isotope
chemist. The reagents below were designed to introduce stable isotopes
using standard chemical procedures.
13 C Labeled Olefi nation Reagents
The 13 C labeled olefi nation reagents 4 were developed to simplify the
labeling process by providing a set of substrates ready to be incorporated
into precedented chemical syntheses. 5 These olefi nation reagents
provide access to a fi xed 13 C label within the alkene as well as site-variable
deuterium incorporation (Scheme 1). This methodology effi ciently
provides a densely labeled compound ready for further functionalization.
O O
S
Ph 13CH
Aldrich.com
CH2
O O
Ph
S
13C
R
R'
K2CO3, CH2O
K2CO3, CD2O
H2O/DMSO
D2O/DMSO O O O
K2CO3, CH2O
S P D2O/DMSO
13CH2 OEt
Ph
OEt
1. K2CO3
H2O/DMSO
2. RI, 3. R'CHO
Scheme 1: Olefi nation reagents labeling strategies.
K 2CO3, CD2O
H 2O/DMSO
O O
Ph
S
13C
D
D D
O O
Ph
S
13C
D
CH2 O O
S
Ph 13CH
The availability of all three sulfur oxidation states allows control of the
reaction conditions including base type and strength as well as access to
a preferred sulfur removal strategy. 6 By providing access to mild reaction
conditions, fewer compatibility issues arise between reaction conditions,
olefi nation reagent and substrate.
New 13 C Labeled Olefi nation Reagents
Ph
O
S P
13CH2 OEt
OEt
Ph
O
S P
13CH2 OEt
OEt
O O O
Ph
S P
13CH2 OEt
OEt
715832 715824
715816
O
Stable Isotopes
Lisa Roth, Ph.D.
Product Manager
lisa.roth@sial.com
D
D
TO ORDER: Contact your local Sigma-Aldrich offi ce (see back cover), or visit Aldrich.com/chemicalsynthesis.
D and/or 13 C Labeled 1,3–Dithiane
Unlabeled 1,3–Dithiane is a versatile reagent able to act as an acyl anion
equivalent when submitted to Corey-Seebach reaction conditions. 7
This well known chemistry can also be carried <strong>out</strong> when 1,3–Dithiane
is labeled at the 2 position providing labeled and protected aldehydes,
ketones, α-hydroxyketones, 1,2–diketones and α-keto acid derivatives.
Deprotection can be facilitated using standard methods to give the
appropriately labeled substrates (Scheme 2). 8
Scheme 2: 1,3–Dithiane for the introduction of D and/or 13 C.
New Labeled D and/or 13 C 1,3–Dithiane
S
13 H
C
H
S
716111
S
13 D
C
D
S
716073
References: (1) Brown, L. D.; Cheung, A.; Harwood, J. E. F.; Battaglia, F. C.; J. Nut. 2009,
139, 1649. (2) Hanke, S.; Besir, H.; Oesterhelt, D.; Mann, M.; J. Proteome. Res. 2008, 7, 1118.
(3) Li, C.; Hill, R.W.; Jones, A. D.; J. Chrom. B 2010, 878, 1809. (4) Licensed from Highlands
Stable Isotopes Corp. (5) a) Capela, R.; Oliveira, R.; Gonçalves, L. M.; Domingos, A; Gut, J.;
Rosenthal, P. J.; Lopes, F.; Moreira, R.; Biorg. Med. Chem. Lett. 2009, 19, 3229. (b) Verissimo,
E.; Berry, N.; Gibbons, P.; Cristiano, M. L. S.; Rosenthal, P. J.; Gut, J.; Ward, S. A.; O’Neill, P. M.;
Biorg. Med. Chem. Lett. 2008, 18, 4210. (6) a) Beye, G. E.; Ward, D. E.; J. Am. Chem. Soc. 2010,
132, 7210. (b) Pellissier, H.; Tetrahedron 2006, 62, 5559. (7) a) Seebach, D.; Corey, E. J.; J. Org.
Chem. 1975, 40, 231. (b) Mundy, P. B.; Ellerd, M. G.; Favaloro, F. G., Jr.; Name Reactions and
Reagents in Organic Synthesis, 2nd ed.; Wiley & Sons: New York, 2005; p 186, 745. (8) Wutz, P.
G. M.; Greene, T. W.; Protection for the Carbonyl Group, Greene’s Protective Groups in Organic
Synthesis, 4th ed.; Wiley & Sons: New York, 2007; p 482.
For more information on these products avaliable from
Aldrich Chemistry, visit Aldrich.com/sinext
or contact:
S
13 R
C
S R
R = H or D
O
O OH
13C R R' O
O
13C R R'
13C R
OH 13C R
R'
O
O
Stable Isotope Technical Services
Phone: (937) 859-1808
(800) 448-9760 (US and Canada)
Fax: (937) 859-4878
E-mail: isosales@sial.com