Fmoc-ThpGly-OH (Fmoc-4-amino-tetrahydropyran-4-carboxylic acid, CAS 285996-72-7) is a specialized Fmoc-protected non-natural amino acid featuring a tetrahydropyran ring fused to the alpha-carbon center. The molecule consists of a rigid six-membered tetrahydropyran (oxane) ring with an amino group at the 4-position, which is protected by the Fmoc (9-fluorenylmethyloxycarbonyl) group, and a carboxylic acid functionality at the same carbon.
Fmoc-ThpGly-OH is a versatile non-natural amino acid building block designed for use in Fmoc solid-phase peptide synthesis (SPPS). The tetrahydropyran ring of Fmoc-ThpGly-OH introduces significant conformational constraint into the peptide backbone, restricting the flexibility of the amino acid residue and potentially enhancing target binding affinity through reduced entropic penalties. The Fmoc protecting group of Fmoc-ThpGly-OH enables standard SPPS deprotection protocols, making it fully compatible with automated peptide synthesizers and routine peptide chemistry workflows. This makes Fmoc-ThpGly-OH an invaluable building block in medicinal chemistry, where the introduction of conformationally constrained non-natural amino acids can improve the potency, selectivity, and metabolic stability of peptide-based therapeutics. For researchers seeking to expand the chemical diversity of their peptide libraries, Fmoc-ThpGly-OH offers a unique sp³-rich scaffold that is underrepresented in traditional peptide screening collections
Product Parameters
Parameter
Specification
Product Name
Fmoc-ThpGly-OH
CAS Number
285996-72-7
Molecular Formula
C₂₁H₂₁NO₅
Molecular Weight
367.40 g/mol
Appearance
White solid
Density
1.35±0.10 g/cm³
Boiling Point
609.9±55.0 °C at 760 mmHg
Storage Condition
Sealed in dry , 2–8 °C
Product Advantages
Conformationally Constrained sp³-Rich Scaffold
Fmoc-ThpGly-OH features a rigid tetrahydropyran ring that restricts the conformational freedom of the amino acid residue. This pre-organization reduces entropic penalties upon receptor binding, potentially enhancing target affinity and selectivity—a property highly valued in medicinal chemistry and drug discovery.
Fully Compatible with Fmoc SPPS
Fmoc-ThpGly-OH is designed for seamless incorporation into Fmoc-based solid-phase peptide synthesis. The Fmoc protecting group enables selective deprotection with piperidine, allowing Fmoc-ThpGly-OH to be used with standard SPPS protocols and automated synthesizers without modification.
Expands Peptide Chemical Diversity
The tetrahydropyran scaffold of Fmoc-ThpGly-OH introduces a sp³-rich, non-natural amino acid that is underrepresented in traditional peptide screening libraries. Incorporating Fmoc-ThpGly-OH into peptide sequences expands the accessible chemical space and can lead to the discovery of novel bioactive compounds with improved pharmaceutical properties.
High Purity with Full Characterization
Cosperpharm supplies Fmoc-ThpGly-OH with ≥98% HPLC purity and full analytical characterization. Each batch is released with a comprehensive COA ensuring batch-to-batch consistency.
Storage Conditions
Store Fmoc-ThpGly-OH in a tightly sealed container at 2–8 °C. Keep the container dry, protected from light, and stored in a clean, well-ventilated area. The compound is hygroscopic; therefore, desiccated storage is recommended and the container should be opened only in a low-humidity environment. Allow the sealed container to reach ambient temperature before opening to minimize moisture condensation.
Handling precautions: Use standard laboratory precautions for handling fine powders. Wear appropriate personal protective equipment (lab coat, safety goggles, chemical-resistant gloves). Avoid generating dust. Use in a well-ventilated area or fume hood.
Application Scenarios
Fmoc SPPS Building
Block Non-natural amino acid building block for incorporation into peptide sequences via Fmoc solid-phase peptide synthesis.
Conformational Constraint Introduction
The tetrahydropyran ring introduces rigidity into peptide backbones, reducing conformational entropy and potentially enhancing target binding affinity.
Medicinal Chemistry & Drug Discovery
Used to expand chemical diversity in peptide libraries and discover novel bioactive compounds with improved pharmacokinetic properties.
Peptide Lead Optimization
Enables structure-activity relationship (SAR) studies through the introduction of constrained non-natural amino acids.
Protein Engineering
Used to introduce non-natural amino acids with defined geometries into engineered proteins.
Advanced Peptide
Therapeutics Contributes to the development of peptide-based therapeutics with enhanced metabolic stability and target selectivity.
Contact Us
Looking for Fmoc-ThpGly-OH to expand your peptide chemistry toolbox? Cosperpharm is your trusted partner for high-quality non-natural amino acids. Reach out today for a quote or to discuss your specific requirements—we're ready to support your research.
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