Description

O-(tert-Butyldimethylsilyl)-N-Fmoc-L-homoserine (CAS: 1333332-17-4) is a high-purity, protected amino acid derivative extensively used in peptide synthesis and solid-phase peptide chemistry. With the molecular formula C₂₅H₃₃NO₅Si, this compound features a tert-butyldimethylsilyl (TBDMS) group protecting the hydroxyl side chain of L-homoserine and an Fmoc (9-fluorenylmethoxycarbonyl) group protecting the α-amino functionality. The TBDMS group ensures stability under basic conditions, while the Fmoc group allows for orthogonal deprotection under mild basic conditions, making it ideal for automated peptide synthesizers. This reagent is particularly valuable in the synthesis of complex peptides, glycopeptides, and other bioactive molecules requiring selective deprotection strategies. Supplied as a white to off-white crystalline powder, it is rigorously tested for purity (typically ≥95% by HPLC) and is suitable for research, pharmaceutical development, and bioconjugation applications. Store under inert conditions at -20°C to maintain stability.

Properties

• CAS Number: 1333332-17-4
• Complexity: 639
• IUPAC Name: (2S)-4-[tert-butyl(dimethyl)silyl]oxy-2-(9H-fluoren-9-ylmethoxycarbonylamino)butanoic acid
• InChI: InChI=1S/C25H33NO5Si/c1-25(2,3)32(4,5)31-15-14-22(23(27)28)26-24(29)30-16-21-19-12-8-6-10-17(19)18-11-7-9-13-20(18)21/h6-13,21-22H,14-16H2,1-5H3,(H,26,29)(H,27,28)/t22-/m0/s1
• InChI Key: LNVNYIRAWWXDCG-QFIPXVFZSA-N
• Exact Mass: 455.21279969
• Molecular Formula: C25H33NO5Si
• Molecular Weight: 455.6
• SMILES: CC(C)(C)[Si](C)(C)OCC[C@@H](C(=O)O)NC(=O)OCC1C2=CC=CC=C2C3=CC=CC=C13
• Topological: 84.9
• Monoisotopic Mass: 455.21279969
• Synonyms: 1333332-17-4, O-(tert-Butyldimethylsilyl)-N-Fmoc-L-homoserine, Fmoc-HomoSer(TBDMS)-OH, (2S)-4-[(tert-butyldimethylsilyl)oxy]-2-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)butanoic acid, (2S)-4-[tert-butyl(dimethyl)silyl]oxy-2-(9H-fluoren-9-ylmethoxycarbonylamino)butanoic acid, (S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-4-((tert-butyldimethylsilyl)oxy)butanoic acid, MFCD30529785, AKOS032455836, AS-67473, DB-101750, CS-0148544, E70926, N-(((9H-Fluoren-9-yl)methoxy)carbonyl)-O-(tert-butyldimethylsilyl)-L-homoserine

Application

O-(tert-Butyldimethylsilyl)-N-Fmoc-L-homoserine is widely employed in solid-phase peptide synthesis (SPPS) as a building block for introducing homoserine residues with orthogonal protection. Its TBDMS group resists cleavage during Fmoc deprotection, enabling sequential assembly of peptides with sensitive functional groups. This compound is also utilized in glycopeptide synthesis, where the protected hydroxyl group can later be glycosylated. Additionally, it serves as a precursor for bioconjugation and proteomics research, particularly in designing peptide-based probes or therapeutics.

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