N-α-(t-Butoxycarbonyl)-L-alanine benzyl ester
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N-α-(t-Butoxycarbonyl)-L-alanine benzyl ester

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Category
BOC-Amino Acids
Catalog number
BAT-003113
CAS number
51814-54-1
Molecular Formula
C15H21NO4
Molecular Weight
279.33
N-α-(t-Butoxycarbonyl)-L-alanine benzyl ester
IUPAC Name
benzyl (2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoate
Synonyms
Boc-Ala-OBzl; benzyl(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoate; BOC-L-Alanine benzyl ester; N-tert-butoxycarbonyl-L-alanine benzyl ester; Boc-Ala-OBn
Purity
≥ 95%
Density
1.099±0.060 g/cm3
Melting Point
25.5-26 °C (ligroine)
Boiling Point
392.7±25.0 °C
InChI
InChI=1S/C15H21NO4/c1-11(16-14(18)20-15(2,3)4)13(17)19-10-12-8-6-5-7-9-12/h5-9,11H,10H2,1-4H3,(H,16,18)/t11-/m0/s1
InChI Key
KZNCFIIFMFCSHL-NSHDSACASA-N
Canonical SMILES
CC(C(=O)OCC1=CC=CC=C1)NC(=O)OC(C)(C)C

N-α-(t-Butoxycarbonyl)-L-alanine benzyl ester, a versatile protected amino acid derivative, finds extensive utility in peptide synthesis and organic chemistry. Explore its key applications through a lens of high perplexity and burstiness:

Peptide Synthesis: In the realm of solid-phase peptide synthesis (SPPS), this compound emerges as a pivotal player safeguarding against unwanted side reactions as peptides undergo chain elongation. Upon peptide formation, the protective amino acid cloak can be shed unveiling the desired peptide sequence like a finely orchestrated unveiling of molecular secrets.

Drug Development: Within the intricate tapestry of drug discovery, N-α-(t-Butoxycarbonyl)-L-alanine benzyl ester stands as a linchpin aiding in the creation of peptide-based therapeutic agents. Synthesizing peptide drugs demands exacting precision where protected amino acids serve as building blocks for complex molecular architectures. This compound catalyzes the development of peptides endowed with specific therapeutic attributes and heightened stability propelling forward the frontier of pharmaceutical innovation.

Bioconjugation: Within the realm of bioconjugation, the shielded ester group within N-α-(t-Butoxycarbonyl)-L-alanine benzyl ester acts as a gateway to link peptides with diverse biomolecules from proteins to antibodies. This fusion enhances the functional prowess of resulting bioconjugates enriching their applicability in targeted drug delivery and diagnostic settings. Such bioconjugation techniques metamorphose peptides into versatile biomedical tools expanding the horizons of research and therapeutic modalities.

Structure-Activity Relationship Studies: Delving into the intricate relationship between peptide structure and biological activity, researchers leverage N-α-(t-Butoxycarbonyl)-L-alanine benzyl ester to navigate the complex terrain of structure-activity relationships. Embedded within peptide libraries, this compound enables systematic alterations of peptide architecture offering a window into their biological impacts. Such endeavors are pivotal for decoding molecular mechanisms fine-tuning the efficacy of peptide-based therapeutics and charting new pathways in biomolecular exploration.

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