Description

(2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-2-methyl-6-(prop-2-enoxycarbonylamino)hexanoic acid is a high-purity, synthetic amino acid derivative designed for advanced peptide synthesis and biochemical research. With a molecular formula of C₂₆H₃₀N₂O₆ and CAS number 1934266-47-3, this Fmoc-protected compound features both an allyloxycarbonyl (Alloc) group and a carboxylic acid functional group, enabling selective deprotection strategies in solid-phase peptide synthesis (SPPS). The stereospecific (S)-configuration at the α-carbon ensures compatibility with chiral peptide sequences, while the 2-methyl substitution introduces steric constraints for structural studies. Supplied as a white to off-white crystalline powder with ≥95% purity (HPLC), this building block is ideal for synthesizing modified peptides, peptidomimetics, and bioconjugates. Store desiccated at -20°C for optimal stability.

Properties

• CAS Number: 1934266-47-3
• Complexity: 706
• IUPAC Name: (2S)-6-(allyloxycarbonylamino)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-2-methyl-hexanoic acid
• InChI: InChI=1S/C26H30N2O6/c1-3-16-33-24(31)27-15-9-8-14-26(2,23(29)30)28-25(32)34-17-22-20-12-6-4-10-18(20)19-11-5-7-13-21(19)22/h3-7,10-13,22H,1,8-9,14-17H2,2H3,(H,27,31)(H,28,32)(H,29,30)/t26-/m0/s1
• InChI Key: MFRYJVYTIOMHGD-SANMLTNESA-N
• Exact Mass: 466.21038668
• Molecular Formula: C26H30N2O6
• Molecular Weight: 466.5
• SMILES: C[C@](CCCCNC(=O)OCC=C)(C(=O)O)NC(=O)OCC1C2=CC=CC=C2C3=CC=CC=C13
• Topological: 114
• Monoisotopic Mass: 466.21038668
• Synonyms: 1934266-47-3, Fmoc-aMeK(Alloc)-OH, EX-A12439, (S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-6-(((allyloxy)carbonyl)amino)-2-methylhexanoic acid

Application

This Fmoc/Alloc-protected amino acid is primarily used in orthogonal peptide synthesis where sequential deprotection of side-chain and α-amino groups is required. The Alloc group can be selectively removed using palladium catalysts without affecting the Fmoc protection, enabling controlled peptide elongation. The methyl group at the α-position is valuable for studying backbone conformational effects in bioactive peptides. Researchers also employ this derivative to introduce allyl-carbamate protected lysine analogs or create branched peptide architectures.

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