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Fmoc-(R)-2-thienylglycine is an R-configured noncanonical amino acid that places a 2-thienyl ring directly at the α-carbon. The thiophene ring provides a compact sulfur-containing aromatic group with different electronics and geometry from phenylalanine-type side chains.
For a Boc-route version of the same R-configured core, compare Boc-(R)-2-thienylglycine. The residue stereochemistry is related, but temporary N-protection and route compatibility differ.
Product Information
| Product Name | Fmoc-(R)-2-thienylglycine |
| Catalog No. | AS4055 |
| CAS No. | 208259-66-9 |
| Molecular Formula | C21H17NO4S |
| Molecular Weight | 379.43 g/mol |
| Building Block Type | Fmoc-protected R-2-thienylglycine |
| Primary Applications | Heteroaromatic peptide SAR; stereochemical analog design; peptidomimetic synthesis; specialized Fmoc-SPPS |
Why Thienylglycine Is Not Phenylalanine
In thienylglycine the heteroaromatic ring is attached directly to the α-carbon rather than through a methylene spacer. This shortens the side-chain reach and changes electronic interactions at the same time.
R Configuration Must Be Verified Separately from Mass
The R and S enantiomers have the same formula and MW. LC-MS can confirm composition but cannot prove which enantiomer is present. CAS, drawn structure, and any available chiral data should be reviewed together.
Coupling and Epimerization Considerations
Aryl glycine derivatives can be sensitive to stereochemical erosion under overly aggressive activation conditions. We recommend minimizing unnecessary preactivation and evaluating the full sequence when high stereochemical fidelity is required.
Procurement and QC Considerations
Matched stereochemical analogs can be prepared through custom peptide synthesis with noncanonical residues.
Product Documents
A Safety Data Sheet (SDS / MSDS) is available for this product to support laboratory handling, storage and safety assessment.
Fmoc-(R)-2-thienylglycine MSDS
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
Can mass spectrometry distinguish R and S thienylglycine?
No. Enantiomers have the same molecular mass.
How is thienylglycine different from phenylalanine?
The heteroaromatic ring is attached directly to the α-carbon and contains sulfur.
Why compare Fmoc and Boc versions?
They offer different temporary N-protection strategies for the same general residue class.
Related Technical Resources
Read about noncanonical amino-acid SAR