(S)-N-Boc-3-Bromophenylalanine
[CAS# 82278-73-7]

Identification

• Classification: Biochemical >> Amino acids and their derivatives >> Phenylalanine derivatives
• Name: (S)-N-Boc-3-Bromophenylalanine
• Synonyms: N-tert-Butoxycarbonyl-3-bromophenyl-L-alanine
• Molecular Formula: C₁₄H₁₈BrNO₄
• Molecular Weight: 344.20
• Protein Sequence: X
• CAS Registry Number: 82278-73-7
• EC Number: 807-895-4
• SMILES: CC(C)(C)OC(=O)N[C@@H](CC1=CC(=CC=C1)Br)C(=O)O

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H315-H319-H332-H335
• Safety Statements: P261-P280-P305+P351+P338

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	4	H332
Acute toxicity	Acute Tox.	4	H302
Skin irritation	Skin Irrit.	2	H315
Specific target organ toxicity - single exposure	STOT SE	3	H335
Eye irritation	Eye Irrit.	2A	H319

Discovery and Applications

(S)-N-Boc-3-bromophenylalanine is a special chemical compound known for its role in peptide synthesis and medicinal chemistry. (S)-N-Boc-3-bromophenylalanine was first synthesized in the early 2000s as part of a broad effort to develop amino acid derivatives with enhanced reactivity and functional diversity. The synthesis involves protecting the amino group with Boc (tert-butyloxycarbonyl) and introducing a bromine atom at the 3-position of the benzene ring. The resulting compound combines the stability of the Boc group with the reactivity of brominated phenylalanine, making it an effective reagent in peptide chemistry.

One of the major uses of (S)-N-Boc-3-bromophenylalanine is in the synthesis of peptides and peptidomimetics. Its bromine atom provides a site for nucleophilic substitution reactions, allowing the incorporation of a variety of functional groups into peptides. This property is essential for the design and optimization of peptides with specific biological activities and improved pharmacological properties.

In medicinal chemistry, (S)-N-Boc-3-bromophenylalanine is used to make peptide-based drugs and therapeutics. The compound's ability to form stable bonds and react selectively can be used to develop drugs that target specific biological pathways or protein interactions. Its role in generating peptide libraries could help discover new therapeutic candidates with enhanced efficacy and selectivity.

Researchers used (S)-N-Boc-3-bromophenylalanine to explore new reaction mechanisms and synthetic approaches. Its unique structure enables the study of various chemical transformations and the development of innovative synthetic strategies. This research helps advance synthetic organic chemistry and create new chemical entities.

References

2017. Lifitegrast. Pharmaceutical Substances.
URL: https://pharmaceutical-substances.thieme.com/ps/search-results?docUri=KD-12-0085