Fmoc-6-(trifluoromethyl)-D-tryptophan (Fmoc-D-Trp(6-CF3)-OH) is an Fmoc-protected D-tryptophan analog bearing a trifluoromethyl group at the indole 6-position. It provides a defined CF3-substituted aromatic residue for Fmoc-SPPS, peptide SAR, and medicinal-chemistry sequence design.

The CF3 substituent adds a larger, strongly electron-withdrawing and lipophilic group than a single fluorine. D stereochemistry adds a second controlled variable beyond the ring substituent and is relevant when backbone recognition or proteolytic susceptibility is being explored. Effects on peptide properties remain sequence-dependent and should be evaluated experimentally.

Product Information

Role of the 6-CF3 Indole Substitution

A CF3 group can change hydrophobic surface area, local electronics, and steric presentation around the indole ring. For matched analog studies, its value is the ability to make a defined side-chain perturbation while keeping the residue recognizable as a tryptophan-derived building block.

Additional aromatic variants can be compared in the aromatic amino acid series.

Coupling and Peptide-Assembly Considerations

The Fmoc group is compatible with routine Fmoc-SPPS, but a bulky CF3-substituted side chain can make local steric effects more relevant in crowded sequences. Coupling completeness should be monitored rather than assumed from the behavior of unmodified tryptophan.

For full-sequence projects containing noncanonical residues, complex peptide synthesis can be evaluated together with the complete protection and QC plan.

Procurement and Identity Control

When no widely accepted CAS assignment is available, identity should be anchored to the complete chemical name, substitution position, stereochemistry, molecular formula, structural record, and lot-specific analytical documentation.

For D/L comparisons, MS confirms mass but not enantiomeric identity. Chiral purity or another stereochemistry-supporting method is preferable when the residue configuration is a critical study variable.

Product Documents

MSDS - Fmoc-6-(trifluoromethyl)-D-tryptophan (AS111)

The Safety Data Sheet provides product identification, hazard information, handling and storage guidance, exposure controls, transport information, and regulatory information for laboratory use.

Certificates of Analysis (COAs) are batch-specific. Please contact us to request the COA for your product, and we will provide it by email.

Frequently Asked Questions

What does Fmoc-D-Trp(6-CF3)-OH identify?

It identifies the Fmoc-protected D-configured amino-acid building block with the defined 6 aromatic substitution pattern.

Can a positional isomer be substituted if the molecular weight is the same?

No. Positional isomers are distinct chemical entities and can produce different peptide properties even when their formulas and nominal molecular weights are identical.

How should D stereochemistry be confirmed?

MS verifies mass but does not distinguish D and L enantiomers. When chirality is experimentally important, review lot-specific chiral purity or equivalent stereochemical documentation.

Research Use Only.