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Description
N-[(9H-Fluoren-9-ylmethoxy)carbonyl]-S-(triphenylmethyl)-L-cysteine, supplied under TCI catalogue code F0652 and known among researchers as Fmoc-Cys(Trt)-OH, is a doubly protected derivative of the amino acid cysteine prepared specifically for peptide synthesis. The alpha-amino group is protected by a fluorenylmethoxycarbonyl group, while the thiol group on the side chain is protected by a trityl group. This material is one of the essential building blocks that any laboratory running solid-phase peptide synthesis must keep on hand, because cysteine is the key amino acid that forms the disulfide bridges determining the three-dimensional structure of peptides and proteins.
The property that makes this derivative a standard choice lies in the orthogonal protection strategy it carries. The Fmoc group can be removed under mild basic conditions using a piperidine solution, so chain elongation proceeds without damaging the side-chain protecting group. Conversely, the trityl group is removed at the final stage under acidic conditions using a mixture of trifluoroacetic acid together with cation scavengers. The bulky trityl protection is also important for preventing oxidation of the thiol to a disulfide before the intended stage, and for suppressing side reactions at the sensitive cysteine side chain during coupling.
In Indonesian laboratories, this reagent is used in university research groups, biotechnology institutes, and pharmaceutical laboratories that build synthetic peptides for study. It is typically ordered alongside other Fmoc-protected amino acids, coupling reagents, and resins to complete a solid-phase peptide synthesis workflow. Analytical and formulation groups also draw on it when preparing peptide standards or cysteine-containing sequences that must later be cyclised through disulfide bond formation.
Laboratory Applications
Solid-phase peptide synthesis: serves as the cysteine building block in Fmoc-based chain assembly, where repeated piperidine deprotection cycles remove the Fmoc group without disturbing the trityl-protected side chain.
Disulfide-bridged peptide preparation: supplies the protected thiol that, after trityl removal with trifluoroacetic acid and scavengers, can be oxidised deliberately to form the disulfide bonds that define peptide folding.
Cyclic peptide construction: allows two cysteine residues to be incorporated at defined positions in a sequence so that an intramolecular disulfide bridge can close the ring under controlled final-stage conditions.
Peptide standard and reference material synthesis: enables laboratories to prepare cysteine-containing sequences in house for analytical comparison, since the orthogonal protection gives reproducible incorporation at each coupling step.
Chemical biology and protein structure studies: provides access to synthetic peptides whose disulfide connectivity can be designed, supporting work on how cysteine residues govern the three-dimensional structure of proteins.
Specifications
Brand: TCI (Tokyo Chemical Industry)
CAS number: 103213-32-7
Catalogue code: F0652
Category: Chemistry > Chemical Biology > Peptide Chemistry
Pack sizes: available in the standard research pack sizes offered by TCI for this catalogue item; please confirm the required size when ordering
Storage note: keep in a cool, dry place in a tightly closed container, protected from moisture and air
Handling and Storage
Store this material in its original tightly closed container in a cool, dry location, away from moisture, direct sunlight, and sources of heat. Amber glass or the manufacturer's supplied packaging is suitable, and the container should be resealed promptly after each use to limit exposure to air, which can promote unwanted thiol oxidation once the protecting group is removed. Handle the solid in a fume hood or well-ventilated area while wearing a laboratory coat, nitrile gloves, and safety goggles, and avoid generating dust during weighing. Deprotection steps involving piperidine or trifluoroacetic acid must always be carried out in a fume hood with appropriate chemical-resistant gloves. Consult the manufacturer's safety data sheet before first use, and dispose of residues and contaminated consumables through the laboratory's chemical waste stream.
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