N-β-(t-Butoxycarbonyl)-γ-(3-thienyl)-L-β-homoalanine
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N-β-(t-Butoxycarbonyl)-γ-(3-thienyl)-L-β-homoalanine

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Category
BOC-Amino Acids
Catalog number
BAT-005207
CAS number
270263-00-8
Molecular Formula
C13H19NO4S
Molecular Weight
285.36
N-β-(t-Butoxycarbonyl)-γ-(3-thienyl)-L-β-homoalanine
IUPAC Name
(3S)-3-[(2-methylpropan-2-yl)oxycarbonylamino]-4-thiophen-3-ylbutanoic acid
Synonyms
Boc-Ala(3-Thienyl)-(C#CH2)OH; (S)-3-[(t-Butoxycarbonyl)amino]-4-(3-thienyl)butanoic acid; Boc-(S)-3-Amino-4-(3-thienyl)butyric acid; N-T-BUTOXYCARBONYL-(S)-3-AMINO-4-(3-THIENYL)BUTANOIC ACID; Boc-(3-thienyl)-L-b-homoalanine; Boc-L-b-HomoAla(3-thienyl)-OH
Appearance
White powder
Purity
≥ 98% (HPLC)
Density
1.216 g/cm3
Boiling Point
452.4±40.0 °C
Storage
Store at 2-8 °C
InChI
InChI=1S/C13H19NO4S/c1-13(2,3)18-12(17)14-10(7-11(15)16)6-9-4-5-19-8-9/h4-5,8,10H,6-7H2,1-3H3,(H,14,17)(H,15,16)/t10-/m0/s1
InChI Key
NMIXJPLQPAOBBV-JTQLQIEISA-N
Canonical SMILES
CC(C)(C)OC(=O)NC(CC1=CSC=C1)CC(=O)O

N-β-(t-Butoxycarbonyl)-γ-(3-thienyl)-L-β-homoalanine (BOC-Thienylalanine) is a protected amino acid derivative used in peptide synthesis and various research applications. Here are some key applications of N-β-(t-Butoxycarbonyl)-γ-(3-thienyl)-L-β-homoalanine:

Peptide Synthesis: BOC-Thienylalanine is commonly used in the chemical synthesis of peptides, where protecting groups like t-butoxycarbonyl are crucial. The BOC group protects the amino functionality during peptide bond formation, ensuring that only the desired sequences are synthesized. After assembly, the protecting group can be removed under mild conditions to yield the free peptide.

Drug Development: BOC-Thienylalanine can be incorporated into peptide-based drug candidates to explore structure-activity relationships. By modifying amino acid sequences with thienylalanine derivatives, researchers can enhance the potency, stability, and selectivity of therapeutic peptides. This approach is valuable in the design of new drugs with improved pharmacological profiles.

Protein Engineering: In protein engineering, BOC-Thienylalanine can be used to introduce non-natural amino acids into proteins. This modification allows scientists to study protein structure and function, as well as to develop proteins with novel properties. The thienyl group can influence the hydrophobicity and electronic properties of the protein, leading to unique biochemical characteristics.

Bioconjugation: BOC-Thienylalanine is helpful in bioconjugation strategies where peptides or proteins are chemically linked to other molecules, such as drugs, fluorescent labels, or biomaterials. The protected amine group can be selectively deprotected and then conjugated to various functional groups. This facilitates the development of targeted therapeutic agents and diagnostic tools.

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