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Description
TCI F0608, bearing CAS number 157355-81-2, is N-[(9H-Fluoren-9-ylmethoxy)carbonyl]-D-threonine: a D-configured threonine whose amine group is protected by an Fmoc group while the side-chain hydroxyl remains free. The material serves as a building block in solid-phase peptide synthesis based on the Fmoc strategy, particularly where researchers require a threonine residue with inverted stereochemistry, or wish to exploit the unprotected hydroxyl group as a site for further reaction. It complements the library of non-natural amino acids needed for the design of modified peptides in natural-product chemistry and medicinal chemistry research laboratories.
The defining characteristic of this material is the presence of two stereogenic centres on the threonine backbone together with a beta-hydroxyl group that is not blocked by a tert-butyl protecting group. This free hydroxyl opens the way to selective reactions such as esterification, glycosylation, or the formation of depsipeptide linkages, but it also demands more careful planning so that side-chain acylation does not occur during coupling. The Fmoc group retains its usual advantages: removal under mild basic conditions and convenient monitoring of reaction progress through the absorbance of the fluorene chromophore. The D configuration imparts distinct conformational and stability behaviour to the resulting peptides.
In Indonesian laboratories, this building block is typically found in research groups working on peptide synthesis within university chemistry departments, medicinal chemistry programmes, and natural-product research units. It is used where standard proteinogenic amino acids are insufficient and the target sequence calls for a non-natural residue. Because the material is consumed on a research rather than production scale, it is generally ordered in quantities matched to a specific synthesis campaign and stored alongside the laboratory's other Fmoc-protected amino acid derivatives.
Laboratory Applications
Fmoc solid-phase peptide synthesis: serves as a direct coupling building block in the standard Fmoc strategy, where its base-labile protecting group is removed under the same mild conditions used for the rest of the sequence.
Incorporation of D-amino acid residues: provides the inverted threonine stereochemistry needed when a research group deliberately designs peptides with altered backbone conformation and different behaviour toward proteolytic degradation.
Depsipeptide construction: the unblocked beta-hydroxyl group can be esterified to form ester linkages in the backbone, making this residue a natural branch point for depsipeptide targets.
Glycopeptide and side-chain modification chemistry: the free hydroxyl offers a defined attachment site for glycosylation or other selective derivatisation without requiring an additional deprotection step beforehand.
Non-natural amino acid library building: expands the in-house collection of protected residues available to medicinal chemistry and natural-product groups designing modified peptide analogues for structure-activity studies.
Specifications
Brand: TCI (Tokyo Chemical Industry)
CAS number: 157355-81-2
Chemical name: N-[(9H-Fluoren-9-ylmethoxy)carbonyl]-D-threonine
Category: Chemistry > Chemical Biology > Peptide Chemistry
Pack sizes: available in the research-scale pack sizes listed in the TCI catalogue for this item
Storage: keep in a cool, dry place in a tightly closed container, following the manufacturer's stated storage condition on the label
Handling and Storage
Store the container tightly closed in a cool, dry, well-ventilated area away from direct sunlight, moisture, and sources of ignition, following the storage condition printed on the manufacturer's label. Keep the material in its original container or in a clean, chemically compatible, tightly sealed vessel, and allow refrigerated stock to reach room temperature before opening to prevent condensation on the solid. Handle in a fume hood using safety glasses, gloves, and a laboratory coat. Weigh out only the amount required and reseal promptly to limit moisture uptake. Consult the supplier's safety data sheet before use, and dispose of residues and contaminated consumables through the laboratory's chemical waste stream in accordance with applicable regulations.
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![N-[(9H-Fluoren-9-ylmethoxy)carbonyl]-D-threonine (CAS 157355-81-2) - TCI F0608 - AMI Scientific](http://amiscientific.com/cdn/shop/files/TCI2510F0608.jpg?v=1769142399&width=1445)
