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Description
TCI catalogue code F0653, Nalpha-[(9H-Fluoren-9-ylmethoxy)carbonyl]-tele-(triphenylmethyl)-L-histidine, is known in most laboratories simply as Fmoc-His(Trt)-OH. It is a protected histidine amino acid derivative designed specifically for solid-phase peptide synthesis using the Fmoc strategy. The alpha-amino group is protected by a fluorenylmethoxycarbonyl group, while the imidazole nitrogen on the side chain is protected by a trityl group. Histidine is a critically important amino acid because its imidazole ring participates in enzyme catalysis, metal ion binding, and pH buffering across the physiological range, which makes the availability of a properly protected form a fundamental requirement for any peptide laboratory.
The properties that have made this derivative a standard choice relate directly to the particular challenges posed by histidine residues. An unprotected imidazole ring is nucleophilic and weakly basic, so it can interfere with coupling reactions and promote racemisation at the histidine residue, which is among the residues most prone to loss of optical purity during synthesis. The bulky trityl group blocks that imidazole nitrogen both sterically and electronically, so the side chain is held inert throughout chain assembly. The orthogonal pairing of a base-labile Fmoc group with an acid-labile trityl group also means the alpha-amino protection can be removed at each cycle without disturbing the side chain, and both protections resolve cleanly at the appropriate stage of the workflow.
In Indonesian laboratories, this derivative is typically used in peptide chemistry and chemical biology groups running Fmoc-based solid-phase synthesis, whether manually on a shaker or on an automated synthesiser. It appears in university research laboratories preparing peptide sequences that contain histidine, in biotechnology and pharmaceutical research units building peptide candidates, and in analytical laboratories preparing peptide reference materials. Because histidine residues are common in biologically active sequences, this building block is usually held as a routine stock item alongside the other protected amino acids.
Laboratory Applications
Fmoc solid-phase peptide synthesis: serves as the standard histidine building block in stepwise chain assembly, where its base-labile alpha protection is removed each cycle without touching the trityl-protected side chain.
Synthesis of metal-binding peptides: supplies histidine residues to sequences designed for coordination of metal ions, since the imidazole ring is the principal metal-coordinating group once the trityl protection has been removed.
Preparation of enzyme-related and catalytic peptide sequences: allows controlled incorporation of the histidine residues that participate in catalytic mechanisms, with the side chain kept inert until the final deprotection step.
Assembly of peptide reference and standard materials: gives analytical laboratories a well-defined protected building block for preparing histidine-containing peptide standards used in method development and verification work.
Automated peptide synthesiser workflows: suits instrument-based synthesis because the trityl protection suppresses side-chain interference and reduces racemisation risk at histidine during repeated automated coupling and deprotection cycles.
Specifications
Brand: TCI
CAS number: 109425-51-6
Category: Chemistry > Chemical Biology > Peptide Chemistry
Common laboratory designation: Fmoc-His(Trt)-OH
Pack sizes: available in the standard catalogue pack sizes offered by TCI for this item; please confirm the size required when ordering.
Storage: store as indicated on the manufacturer's label for this product.
Handling and Storage
Store the container tightly closed in a cool, dry place, protected from moisture and away from direct sunlight, following the storage conditions stated on the manufacturer's label. Keep the material in its original supplier container, or in a clean, well-sealed glass or chemically compatible container that is clearly labelled with the product name and catalogue code. Allow refrigerated material to reach room temperature before opening to prevent condensation on the solid. Handle in a fume hood using gloves, safety glasses, and a laboratory coat, weigh out portions with clean dry spatulas to avoid contaminating the bulk stock, and consult the manufacturer's safety data sheet before use and for disposal guidance.
![Nalpha-[(9H-Fluoren-9-ylmethoxy)carbonyl]-tele-(triphenylmethyl)-L-histidine (CAS 109425-51-6) - TCI F0653 - AMI Scientific](http://amiscientific.com/cdn/shop/files/TCI2510F0653.jpg?v=1768360191&width=1946)
![Nalpha-[(9H-Fluoren-9-ylmethoxy)carbonyl]-tele-(triphenylmethyl)-L-histidine (CAS 109425-51-6) - TCI F0653 - AMI Scientific](http://amiscientific.com/cdn/shop/files/TCI2510F0653.jpg?v=1768360191&width=1445)
