Description

(R)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-4-(((benzyloxy)carbonyl)amino)butanoic acid (CAS No. 387824-79-5) is a high-purity, protected amino acid derivative designed for peptide synthesis and biochemical research. This compound features dual protection with Fmoc (9-fluorenylmethoxycarbonyl) and Cbz (benzyloxycarbonyl) groups, ensuring selective deprotection during solid-phase peptide synthesis (SPPS). Its molecular formula, C₂₇H₂₆N₂O₆, offers precise compatibility with automated synthesizers. Ideal for researchers developing therapeutic peptides or studying post-translational modifications, this product is rigorously tested via HPLC, NMR, and MS to guarantee ≥95% purity. Store desiccated at -20°C for optimal stability.

Properties

• CAS Number: 387824-79-5
• Complexity: 702
• IUPAC Name: (2R)-4-(benzyloxycarbonylamino)-2-(9H-fluoren-9-ylmethoxycarbonylamino)butanoic acid
• InChI: InChI=1S/C27H26N2O6/c30-25(31)24(14-15-28-26(32)34-16-18-8-2-1-3-9-18)29-27(33)35-17-23-21-12-6-4-10-19(21)20-11-5-7-13-22(20)23/h1-13,23-24H,14-17H2,(H,28,32)(H,29,33)(H,30,31)/t24-/m1/s1
• InChI Key: VHBSCTCUNZLWCT-XMMPIXPASA-N
• Exact Mass: 474.17908655
• Molecular Formula: C27H26N2O6
• Molecular Weight: 474.5
• SMILES: C1=CC=C(C=C1)COC(=O)NCC[C@H](C(=O)O)NC(=O)OCC2C3=CC=CC=C3C4=CC=CC=C24
• Topological: 114
• Monoisotopic Mass: 474.17908655
• Synonyms: 387824-79-5, FMOC-D-DAB(Z)-OH, (R)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-4-(((benzyloxy)carbonyl)amino)butanoic acid, (2R)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-4-(phenylmethoxycarbonylamino)butanoic acid, MFCD02684372, N-FMOC-N’-CBZ-D-2,4-DIAMINOBUTYRIC ACID, DTXSID50678758, AKOS016842924, BS-49034, CS-0435006, S-387824-79-5, (2R)-4-{[(Benzyloxy)carbonyl]amino}-2-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)butanoic acid, N-alpha-(9-Fluorenylmethyloxycarbonyl)-N-gamma-(benZyloxycarbonyl)-D-2,4-diaminobutyric acid (Fmoc-D-Dab(CbZ)-OH)

This compound is primarily used in peptide synthesis, particularly for introducing D-2,4-diaminobutyric acid (D-Dab) residues with orthogonal protection. It enables controlled elongation of peptide chains in Fmoc-based SPPS, with applications in antibiotic development (e.g., peptidomimetics) and neuroscience research (neuroactive peptide analogs). The Cbz group allows selective side-chain deprotection while maintaining Fmoc on the α-amine.

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