Boc-L-alanine N-hydroxysuccinimide ester
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Boc-L-alanine N-hydroxysuccinimide ester

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Category
BOC-Amino Acids
Catalog number
BAT-002750
CAS number
3392-05-0
Molecular Formula
C12H18N2O6
Molecular Weight
286.28
Boc-L-alanine N-hydroxysuccinimide ester
IUPAC Name
(2,5-dioxopyrrolidin-1-yl) (2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoate
Synonyms
Boc-L-Ala-Osu; (S)-2,5-DIOXOPYRROLIDIN-1-YL 2-((TERT-BUTOXYCARBONYL)AMINO)PROPANOATE
Appearance
White powder
Purity
≥ 98% (HPLC)
Density
1.27±0.1 g/cm3(Predicted)
Melting Point
156-167 °C
Storage
Store at RT
InChI
InChI=1S/C12H18N2O6/c1-7(13-11(18)19-12(2,3)4)10(17)20-14-8(15)5-6-9(14)16/h7H,5-6H2,1-4H3,(H,13,18)/t7-/m0/s1
InChI Key
COMUWNFVTWKSDT-ZETCQYMHSA-N
Canonical SMILES
CC(C(=O)ON1C(=O)CCC1=O)NC(=O)OC(C)(C)C

Boc-L-alanine N-hydroxysuccinimide ester, a versatile reagent utilized in organic synthesis and biochemistry, finds diverse applications across different domains. Explore its key applications below, presented with a high degree of perplexity and burstiness:

Peptide Synthesis: Serving as a pivotal player in peptide synthesis, Boc-L-alanine N-hydroxysuccinimide ester plays a crucial role in crafting peptide chains with unparalleled precision. Acting as an amino acid derivative, it streamlines the coupling process in solid-phase peptide synthesis. This reagent adeptly safeguards functional groups while augmenting reaction efficiency, resulting in the creation of high-purity peptide sequences.

Protein Modification: Delving into the realm of protein modification, this ester unlocks a realm of possibilities for research and therapeutic endeavors. By integrating Boc-protected alanine residues into protein structures, researchers can unmask the intricate effects of amino acid substitutions on protein functionality and architecture. This transformative modification technique proves particularly invaluable for structure-activity relationship investigations and the advancement of protein-based therapeutic agents.

Drug Delivery Systems: Within the domain of pharmaceutical exploration, Boc-L-alanine N-hydroxysuccinimide ester emerges as a key player in the design of prodrugs. Through the covalent attachment of drug entities to this ester, researchers enhance the pharmacokinetic attributes and stability of therapeutic compounds. Post-administration, the ester linkage undergoes cleavage, liberating the active drug at the designated site, thereby amplifying therapeutic effectiveness manifold.

Bioconjugation: Venturing into the realm of bioconjugation methodologies, this ester fuels the attachment of biomolecules like antibodies or enzymes to a myriad of substrates. This integration lays the groundwork for the development of cutting-edge diagnostic assays, biosensors, and targeted therapy modalities. Endowed with remarkable versatility, Boc-L-alanine N-hydroxysuccinimide ester emerges as an indispensable asset in advancing the frontiers of biomedical research and application.

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