(R)-3-Aminotetrahydrofuran-3-carboxylic acid

(R)-3-Aminotetrahydrofuran-3-carboxylic acid (CAS 1315053-78-1) is a chiral, non-proteinogenic, Cα-tetrasubstituted cyclic amino acid characterized by a tetrahydrofuran ring with geminal amine and carboxylic acid substituents at the 3-position. The molecule features a five-membered oxygen-containing heterocycle (tetrahydrofuran) that serves as the core scaffold, with an amino group (-NH₂) and a carboxylic acid (-COOH) both attached to the same carbon at the 3-position of the ring.

(R)-3-Aminotetrahydrofuran-3-carboxylic acid is a specialized chiral amino acid building block that has garnered significant attention in peptide chemistry, drug discovery, and medicinal chemistry due to its unique Cα-tetrasubstituted cyclic structure. As a non-proteinogenic amino acid, (R)-3-Aminotetrahydrofuran-3-carboxylic acid offers properties that cannot be achieved with standard α-amino acids: the tetrahydrofuran ring imposes significant conformational constraint on peptide backbones, making it an invaluable tool for foldamer design and the development of conformationally defined bioactive peptides. The geminal amine and carboxylic acid substituents at the 3-position enable standard peptide coupling chemistry while the rigid ring system locks the molecule in a defined conformation.

In pharmaceutical research, (R)-3-Aminotetrahydrofuran-3-carboxylic acid serves as an essential intermediate in the synthesis of next-generation small-molecule therapeutics. The compound’s (R)-configuration is critical for biological activity in certain applications, as the corresponding (S)-enantiomer has been identified as the biologically active form in Factor Xa inhibition programs, leaving the (R)-enantiomer as either inactive or an essential stereochemical comparator. This stereospecificity underscores the importance of enantiopure (R)-3-Aminotetrahydrofuran-3-carboxylic acid in drug discovery programs where stereochemistry dictates biological outcomes.

Product Parameters

Why Cosperpharm?

When your peptide synthesis, foldamer design, or drug discovery program demands a reliable source of conformationally constrained amino acids, Cosperpharm delivers (R)-3-Aminotetrahydrofuran-3-carboxylic acid with the quality, documentation, and technical support that research professionals require.

Conformational constraint begins here. The Cα-tetrasubstituted cyclic structure of (R)-3-Aminotetrahydrofuran-3-carboxylic acid is what makes it unique — the rigid tetrahydrofuran ring locks the peptide backbone into defined conformations that cannot be achieved with standard amino acids. Any impurity or incorrect stereochemistry in this building block will propagate through your peptide sequence and compromise your conformational analysis or biological results. Cosperpharm’s analytical release protocol includes HPLC purity verification, chiral HPLC for enantiomeric excess confirmation, and structural identity confirmation — because your peptide conformation depends on the quality of this building block.

Documentation that supports your research. Every shipment of (R)-3-Aminotetrahydrofuran-3-carboxylic acid includes a Certificate of Analysis (COA) with batch-specific purity data, chromatographic profiles, and identity confirmation. For customers requiring additional documentation for regulatory submissions or quality systems, Cosperpharm provides custom quality agreements, stability summaries, and analytical data packages upon request.

Flexible supply across all research scales. Cosperpharm supplies (R)-3-Aminotetrahydrofuran-3-carboxylic acid across the full range of applications — from 10 mg–100 mg quantities for early-stage peptide synthesis and conformational studies, to gram-scale batches for process development and preclinical studies, to bulk quantities for larger production needs. R&D samples ship within 5–7 business days.

Technical support from peptide chemistry experts. Our team can advise on peptide coupling conditions, compatibility with standard Fmoc solid-phase peptide synthesis, analytical methods for monitoring incorporation efficiency, and strategies for optimizing peptide conformation — because we understand the unique challenges of working with constrained amino acids.

Global reach with transparent communication. Cosperpharm ships to pharmaceutical companies, biotechnology firms, CROs, and academic institutions worldwide. We communicate lead times and availability upfront — no surprises, no hidden fees.

Product Advantages

(R)-3-Aminotetrahydrofuran-3-carboxylic acid is a rare Cα-tetrasubstituted cyclic amino acid where the α-carbon bears both the amino and carboxyl groups as well as two ring bonds. This structural feature imposes significant conformational constraint on peptide backbones, making it invaluable for foldamer design and the development of conformationally defined bioactive peptides.

 Defined (R)-Stereochemistry with Distinct Biological Activity

The (R)-configuration of (R)-3-Aminotetrahydrofuran-3-carboxylic acid is critical for certain applications, as the corresponding (S)-enantiomer is utilized in entirely different pharmacological contexts. In peptide engineering, the chirality at the Cα position is the sole determinant of whether a peptide adopts a critical β-turn conformation. Using a racemate or the wrong enantiomer would invalidate your experimental results.

 Rigid Tetrahydrofuran Ring Enhances Peptide Stability

The tetrahydrofuran ring introduces conformational rigidity that can improve proteolytic stability and enhance target binding affinity through reduced entropic penalties. This makes (R)-3-Aminotetrahydrofuran-3-carboxylic acid an ideal building block for designing metabolically stable peptide therapeutics.

 Versatile Building Block for Multiple Applications

(R)-3-Aminotetrahydrofuran-3-carboxylic acid serves as an essential intermediate in the synthesis of next-generation small-molecule therapeutics and is widely used in peptide chemistry, conformational analysis, and foldamer design. Its applications span drug discovery, chemical biology, and materials science.

 Reliable Supply with Established Synthetic Routes

The compound benefits from established synthetic routes that ensure consistent quality and enantiopurity. Cosperpharm’s manufacturing processes are validated to deliver (R)-3-Aminotetrahydrofuran-3-carboxylic acid with ≥95% purity and reliable enantiomeric excess, batch after batch.

 FAQ

A: The (R)-enantiomer (CAS 1315053-78-1) and (S)-enantiomer (CAS 1315052-80-2) are stereoisomers with different biological activities. In peptide engineering, the chirality at the Cα position determines whether a peptide adopts a critical β-turn conformation. Using a racemate or the wrong enantiomer would invalidate experimental results.

Q2: What are the primary applications of this compound?

A: (R)-3-Aminotetrahydrofuran-3-carboxylic acid is used in peptide chemistry, conformational analysis, foldamer design, and as an intermediate in the synthesis of small-molecule therapeutics.

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