$275.00 - $827.00
Fmoc-N-Me-HomoPhe-OH combines N-methylation with the extended hydrophobic side chain of L-homophenylalanine. Relative to phenylalanine, the phenyl ring is separated from the alpha carbon by an additional methylene group.
That extra methylene and the N-methyl substituent affect different parts of the molecule: HomoPhe changes side-chain reach and hydrophobic packing, while N-methylation changes backbone hydrogen bonding and steric demand.
Product Information
| Product Name | Fmoc-N-Me-HomoPhe-OH |
| Catalog No. | AS2098 |
| CAS No. | 1065076-30-3 |
| Molecular Formula | C26H25NO4 |
| Molecular Weight | 415.49 g/mol |
| Building Block Type | Fmoc-protected N-methyl-L-homophenylalanine |
| Primary Applications | Backbone N-methylation; hydrophobic peptide SAR; macrocycle design; conformational tuning; specialized Fmoc-SPPS |
HomoPhe Changes Side-Chain Reach
The additional methylene moves the aromatic ring farther from the peptide backbone. This can improve or weaken hydrophobic contacts depending on the target pocket and can also change RP-HPLC retention of the final peptide.
N-Methylation Changes the Backbone
The N-methyl group removes one backbone N-H donor and can favor different local conformations. In macrocycles, these effects can contribute to permeability or conformational preorganization, but the outcome is sequence-dependent.
Coupling Difficulty Is a Real Procurement Variable
N-methylated residues frequently require more attention during coupling than standard amino acids. If the final sequence also contains other sterically demanding residues, review the common side reactions and difficult-coupling guide before assuming a standard SPPS cycle will be sufficient.
Use in Peptide SAR
This building block is most useful when both backbone N-methylation and aromatic side-chain extension are intentional SAR variables. Alan Scientific's noncanonical amino-acid overview discusses how these modifications expand peptide chemical space.
Procurement and QC Considerations
Confirm CAS 1065076-30-3, C26H25NO4, MW 415.49 g/mol and S/L stereochemistry. For peptides containing multiple N-methyl residues, coupling strategy can be evaluated through custom noncanonical peptide synthesis.
Product Documents
A Safety Data Sheet (SDS / MSDS) is available for this product to support laboratory handling, storage and safety assessment.
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
How is HomoPhe different from Phe?
Homophenylalanine contains one extra methylene between the alpha carbon and phenyl ring.
What does N-Me change?
It methylates the peptide backbone nitrogen, removing one N-H donor and increasing steric bulk.
Can standard Fmoc-SPPS be used?
Yes, but N-methyl residues can require more demanding coupling conditions.
Related Technical Resources
Explore noncanonical peptide design