Description

(2S)-3-carbamoyl-2-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)-2-methylpropanoic acid (CAS: 1403590-49-7) is a high-purity, synthetic amino acid derivative designed for advanced peptide synthesis and biochemical research applications. This compound features a 9H-fluoren-9-ylmethoxycarbonyl (Fmoc) protecting group, ensuring compatibility with solid-phase peptide synthesis (SPPS) protocols. Its molecular formula, C₂₀H₂₀N₂O₅, and precise stereochemistry (2S-configuration) make it ideal for constructing chiral peptides with controlled structural integrity. The inclusion of a carbamoyl group enhances its utility in post-synthetic modifications. Packaged under inert conditions to ensure stability, this product is rigorously tested via HPLC, NMR, and mass spectrometry to meet the highest standards for researchers in medicinal chemistry and proteomics.

Properties

• CAS Number: 1403590-49-7
• Complexity: 573
• IUPAC Name: (2S)-4-amino-2-(9H-fluoren-9-ylmethoxycarbonylamino)-2-methyl-4-oxo-butanoic acid
• InChI: InChI=1S/C20H20N2O5/c1-20(18(24)25,10-17(21)23)22-19(26)27-11-16-14-8-4-2-6-12(14)13-7-3-5-9-15(13)16/h2-9,16H,10-11H2,1H3,(H2,21,23)(H,22,26)(H,24,25)/t20-/m0/s1
• InChI Key: WDVALBSODAWGFX-FQEVSTJZSA-N
• Exact Mass: 368.13722174
• Molecular Formula: C20H20N2O5
• Molecular Weight: 368.4
• SMILES: C[C@](CC(=O)N)(C(=O)O)NC(=O)OCC1C2=CC=CC=C2C3=CC=CC=C13
• Topological: 119
• Monoisotopic Mass: 368.13722174
• Synonyms: 1403590-49-7, (2S)-3-carbamoyl-2-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)-2-methylpropanoic acid, (2S)-3-carbamoyl-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-2-methylpropanoic acid, 978-656-0, (S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-4-amino-2-methyl-4-oxobutanoic acid, FMoc-a-Me-Asn-OH, FMoc-alpha-Me-Asn-OH, (2S)-4-amino-2-(9H-fluoren-9-ylmethoxycarbonylamino)-2-methyl-4-oxobutanoic acid, MFCD28167050, FMoc-|A-Me-Asn-OH, (S)-2-(Fmoc-amino)-4-amino-2-methyl-4-oxobutanoic acid, FMOC-ALFA-ME-ASN-OH, FF72781, AS-77928, CS-0186154, F15990, (S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-4-amino-2-methyl-4-oxobutanoicacid

Application

This Fmoc-protected amino acid derivative is widely used in peptide synthesis, particularly for introducing methyl-substituted chiral centers into peptide chains. It serves as a key building block in the development of therapeutic peptides and bioconjugates, enabling precise control over peptide backbone modifications. Researchers also employ it in structure-activity relationship (SAR) studies to investigate steric and electronic effects in bioactive peptides.

Safety and Hazards

GHS Hazard Statements

• H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]
• H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]
• H335 (100%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]

Precautionary Statements

• P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501

Hazard Classes and Categories

• Skin Irrit. 2 (100%)
• Eye Irrit. 2A (100%)
• STOT SE 3 (100%)

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Disclaimer: Sold exclusively for laboratory research. Prohibited for commercial use, diagnostics, or human/animal applications. Buyers assume all compliance liability.