Description

(2S,3R)-Fmoc-3-Hydroxy-Phenylalanine is a non-natural, ortho-substituted amino acid derivative protected with a fluorenylmethyloxycarbonyl (Fmoc) group, serving as a critical chiral building block in solid-phase peptide synthesis (SPPS). Its unique stereochemistry and phenolic hydroxyl group make it essential for introducing specific structural motifs and post-translational modification analogs into synthetic peptides. This high-purity intermediate is primarily utilized by research institutions and pharmaceutical companies engaged in the development of novel peptide-based therapeutics, diagnostics, and biochemical tools.

Application

• Solid-Phase Peptide Synthesis (SPPS): As a protected amino acid for the automated synthesis of complex peptides containing ortho-tyrosine or modified phenylalanine residues.
• Pharmaceutical Research: Incorporation into peptide drug candidates to study structure-activity relationships (SAR), enhance stability, or mimic natural post-translational modifications like phosphorylation.
• Bioconjugation & Probe Development: Used to synthesize peptide tags or linkers with a reactive phenolic group for subsequent labeling with fluorescent dyes, biotin, or other reporter molecules.
• Chemical Biology: Synthesis of peptide substrates or inhibitors for enzyme studies, particularly those involving kinases, phosphatases, or redox enzymes.
• Material Science: Building block for the synthesis of peptide-based biomaterials and hydrogels, where the hydroxyl group can participate in cross-linking or functionalization.

Basic Information

Product Name	(2S,3R)-Fmoc-3-Hydroxy-Phenylalanine
CAS No.	197458-39-2
Molecular Formula	C24H21NO5
Molecular Weight	403.43 g/mol
Synonyms	Fmoc-(2S,3R)-3-hydroxy-phenylalanine; (2S,3R)-2-(((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-3-(2-hydroxyphenyl)propanoic acid; Fmoc-o-Tyr-OH (stereospecific); Fmoc-3-hydroxy-D-phenylalanine (2S,3R); N-[(9H-Fluoren-9-ylmethoxy)carbonyl]-3-hydroxy-D-phenylalanine; (2S,3R)-N-Fmoc-3-(2-hydroxyphenyl)alanine; ortho-Fmoc-tyrosine (specified isomer)
EINECS	Contact for details

Quality Control

Our (2S,3R)-Fmoc-3-Hydroxy-Phenylalanine is manufactured under strict quality management systems. Each batch undergoes comprehensive analytical testing, including chiral purity verification by HPLC, to ensure it meets the high standards required for advanced peptide synthesis. A detailed Certificate of Analysis (COA) providing batch-specific data for identity, purity, and chiral excess is provided with every shipment.

Storage

Preserve in a tightly closed container, protected from light. Store in a cool, dry place at 15-25°C. This compound is hygroscopic (moisture-sensitive); desiccants are recommended for long-term storage. Keep container tightly sealed when not in use to minimize exposure to atmospheric moisture.

Specification

Item	Specification
Appearance	White to off-white powder
Identification (IR)	Conforms to structure
Purity (HPLC)	≥ 98.0%
Chiral Purity (HPLC)	≥ 99.0% de
Water Content (KF)	≤ 1.0%
Heavy Metals	≤ 20 ppm

Note: Specifications can be tailored. Please contact us for the detailed technical data sheet of a specific grade.