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3’ Thiol, 3’-Thiol-modifier C6

S-S CPG

Box 1 | Product List


Beaucage SL. Strategies in the preparation of DNA oligonucleotide
3’ Thiol-Modifier C6 S-S CPG arrays for diagnostic applications. Curr Medicinal Chem, 8, 1213-1244.
(2001)
Cat. No. Amount
AHP-CH-TC60100 100 mg Gorodetsky AA, Barton JK. Electrochemistry using self-assembled DNA
monolayers on highly oriented pyrolytic graphite. Langmuir, 22, 7917-
AHP-CH-TC61000 1000 mg
7922. (2006)

Liu RH, Coty WA, Reed MW, Gust G. Electrochemical detection-based


DNA microarrays, IVD Tech, 31. (2008)
Name: 3’-Thiol-modifier C6 S-S CPG
Chemical Name: 1-O-Dimethoxytrityl-hexyl-disulfide,1’-succi- Umek RM, Lin SW, Vielmetter J, Terbrueggen RH, Yu CJ, Kayyem JF,
noyl-long chain alkylamino-CPG Irvine B, Yowanto H, Blackburn GF, Farkas DH, Chen YP. Electronic
Formula: N/A detection of nucleic acids: a versatile platform for molecular diagnostics.
J Mol Diagn, 3, 74-84. (2001)

Use: 3’-Thiol-modifier C6 S-S CPG is used to label a thiol group Lockett, MR, Phillips, MF, Jarecki, JL, Peelen, D, Smith LM. A tetrafluo-
at the 3’ end of oligonucleotides. rophenol activated ester self-assembled monolayer for the immobiliza-
Purity: 95%+ tion of amine-modified oligonucleotides. Langmuir, 24 (1), 69-75. (2008)
Diluent: Anhydrous Acetonitrile
Stability in Solution: N/A Wei F, Wang J, Liao W, Zimmermann BG, Wong DT, Ho CM. Electro-
chemical detection of low-copy number salivary RNA based on specific
Background: signal amplification with a hairpin probe. Nucleic Acids Res, 36(11), e65.
(2008)
Thiol modifications are important in the production of diagnos-
tic probes. They are use in DNA synthesizers to functionalize Frutos AG, Brockman JM, Corn RM. Reversible protection and reactive
oligonucleotides. The terminal thiol group allows attachment of patterning of amine and hydroxyl-terminated self-assembled monolay-
an oligo to various ligands, such as biotin, alkaline phosphatase ers on gold surfaces for the fabrication of biopolymer arrays. Langmuir,
or fluorescent dyes. Via an iodoacetamide or maleimide link- 16, 2192-2197. (2000)
age, it allows for the attachment of an oligo to a solid surface.
Thiol modification can be placed at either the 5’ or 3’ end of the Liepold P, Kratzmüller T, Persike N, Bandilla M, Hinz M, Wieder H,
oligonucleotide. For introduction of a thiol group at the 3’-end, Hillebrandt H, Ferrer E, Hartwich G. Electrically detected displacement
thiol-modifier C6 S-S CPG is available. To introduce a thiol assay (EDDA): a practical approach to nucleic acid testing in clinical or
group at the 5’ end, either 5’-thiol-modifier-C6 or 5’-thiol modi- medical diagnosis. Anal Bioanal Chem, 391, 1759-72. (2009)
fier C6 S-S may be used.
Li Z, Jin R, Mirkin CA, Letsinger RL. Multiple thiol-anchor capped DNA-
Coupling: All oxidation steps should use 0.02M Iodine solution gold nanoparticle conjugates. Nucleic Acids Res., 30, 1558-62. (2002)
to avoid oxidative cleavage of the disulfide linkage.
Demers LM, Mirkin CA, Mucic RC, Reynolds RA III, Letsinger RL.
Deprotection: After proceeding with normal deprotection, the Fluorescence-based method for determining the surface coverage and
disulfide can be cleaved at room temperature in 30 minutes with hybridization efficiency of thiol-capped oligonucleotides bound to gold
a buffered 100 mM DTT pH 8.3 - 8.5 solution. It is imporant to thin films and nanoparticles. Anal Chem, 72, 5535–5541. (2000)
completely remove the reducing agent before using the oligo in
a coupling reaction. Letsinger RL, Elghanian R, Viswanadham G, Mirkin CA. Use of a ster-
oid cyclic disulfide anchor in constructing gold nanoparticle-oligonucleo-
Storage: Freezer storage, -10 to -30°C, dry, dark area tide conjugates,” Bioconjugate Chem, 11(2), 289–291. (2000)

Labeled Oligo Storage: Store labeled oligo in the dark, either


dry or in a neutral aqueous media at -20°C. Do not store crude
fluorescently labeled oligonucleotides using ammonia.

MSDS: www.allelebiotech.com

Reference:

Phillips MF, Lockett MR, Rodesch MJ, Shortreed MR, Cerrina F, Smith
LM. In situ oligonucleotide synthesis on carbon materials: stable sub-
strates for microarray fabrication. Nucleic Acids Res, 36, e7. (2008)

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