Thiol-Modifier C6 S-S Phosphoramidite
Oligonucleotide Conjugation & Delivery Ligands
Product summary
Quick view
- Product family
- Oligonucleotide Conjugation & Delivery Ligands
- MF
- C42H61N2O5PS2
- MW
- 769.1
- Purity
- >=99% (HPLC)
Thiol-Modifier C6 S-S Phosphoramidite is a non-nucleoside modifier for adding a reactive thiol group to an oligonucleotide: a six-carbon linker terminating in a disulfide (S-S)-protected thiol, with a 5'-O-(4,4'-dimethoxytrityl) handle and a (2-cyanoethyl N,N-diisopropyl)phosphoramidite. Its PubChem-backed identity includes CAS 148254-21-1, molecular formula C42H61N2O5PS2, molecular weight 769.1, and PubChem CID 15409186.
Coupling attaches the linker to the oligonucleotide (typically the 5'-terminus). The thiol is carried as an internal disulfide during synthesis; reducing the disulfide afterward (e.g. with a thiol reducing agent) reveals a free sulphydryl group on a C6 spacer. That thiol can then be derivatised with thiol-specific probes such as maleimides or iodoacetates.
Synonyms
5'-Thiol-Modifier C6 S-S; DMT-protected hexyl disulfide thiol linker phosphoramidite
Identity and specifications
| Catalog No. | CH65106 |
| CAS No. | 148254-21-1 |
| Molecular Formula | C42H61N2O5PS2 |
| Molecular Weight | 769.1 |
| PubChem CID | 15409186 |
| InChIKey | VEONRKLBSGQZRU-UHFFFAOYSA-N |
| Purity | >=99% (HPLC) |
Storage conditions
-20 C
Technical attributes
- Modifier type
- Non-nucleoside thiol-modifier phosphoramidite
- Spacer
- C6 (hexyl)
- Protected handle
- Disulfide-protected thiol
- Exposed handle
- Thiol after disulfide reduction
- Grade
- N (Normal)
- Packaging
- 10 mg; 25 mg; 50 mg; 100 mg; 200 mg; 250 mg; 500 mg; 1 g; 2 g; 5 g; 10 g; 25 g; 50 g; 100 g; 500 g; 1 kg; 10 kg; 25 kg; 100 µmol; Custom packaging on request
- Water content
- <=0.5%
- Physical form
- colorless oily liquid
- Stability
- Solution: 2-3 days; SDS: stable
Application context
- Thiol conjugation handle: provides a thiol on a six-carbon spacer at the oligonucleotide terminus for thiol-specific coupling.
- Disulfide-protected: the thiol is carried as an S-S disulfide during synthesis and revealed by reduction afterward.
- Reacts with thiol-specific probes: the free thiol conjugates with maleimides, iodoacetates, and similar thiol-reactive reagents.
Related technical resources
Hepatocyte-Targeted Delivery
GalNAc ligands, oligo conjugation handles, lipid conjugates, and linker choices for liver-directed delivery research.
GalNAc vs Lipid Conjugation
Compare receptor-directed multivalent GalNAc and structure-dependent lipid conjugation as distinct oligonucleotide delivery strategies.
Public references
- Targeted delivery of antisense oligonucleotides to hepatocytes using triantennary N-acetyl galactosamine improves potency in mice
Nucleic Acids Research, 2014
Product-family technical context
- Multivalent N-acetylgalactosamine-conjugated siRNA localizes in hepatocytes and elicits RNAi-mediated gene silencing
Journal of the American Chemical Society, 2014
Product-family technical context
- siRNA Conjugates Carrying Sequentially Assembled Trivalent N-Acetylgalactosamine Linked Through Nucleosides Elicit Robust Gene Silencing In Vivo in Hepatocytes
ACS Chemical Biology, 2015
Product-family technical context
- Comparative Characterization of Hepatic Distribution and mRNA Reduction of Antisense Oligonucleotides Conjugated with Triantennary N-Acetyl Galactosamine and Lipophilic Ligands
Journal of Pharmacology and Experimental Therapeutics, 2016
Product-family technical context
- PubChem Compound 15409186
PubChem · CID 15409186
Frequently Asked Questions
What does the Thiol-Modifier C6 S-S do?
It provides a thiol group on a six-carbon spacer at an oligonucleotide terminus. The thiol is protected as a disulfide during synthesis; after reduction, the free thiol can be conjugated with thiol-specific probes such as maleimides or iodoacetates.
Why is the thiol supplied as a disulfide (S-S)?
A free thiol is reactive and prone to oxidation, so this modifier carries the thiol in disulfide-protected form during synthesis. Reducing the disulfide afterward reveals the free sulphydryl group for conjugation.
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