55533-24-9

Basic information

• Product Name: Boc-4-Amino-L-phenylalanine
• Synonyms: RARECHEM BK PT 0173;(S)-2-(TERT-BUTOXYCARBONYLAMINO)-3-(4-AMINOPHENYL)PROPANOIC ACID;N-ALPHA-TBOC-P-AMINO-L-PHENYLALANINE;N-ALPHA-TERT-BUTYLOXYCARBONYL-4-AMINO-L-PHENYLALANINE;N-ALPHA-T-BUTOXYCARBONYL-L-P-AMINO-PHENYLALANINE;N-ALPHA-T-BUTOXYCARBONYL-L-(4-AMINO)-PHENYLALANINE;N-BOC-4-AMINO-L-PHENYLALANINE;4-AMINO-N-TERT-BUTOXYCARBONYL-PHENYLALANINE
• CAS NO: 55533-24-9
• Molecular Formula: C₁₄H₂₀N₂O₄
• Molecular Weight: 280.32
• Product Categories: Phenylalanine analogs and other aromatic alpha amino acids;Amino Acids;Phenylalanine [Phe, F];Unusual Amino Acids;Boc-Amino acid series;a-amino
• Mol File: 55533-24-9.mol
• Article Data: 12

Chemical Properties

• Melting Point: 124-126℃
• Boiling Point: 484.9 °C at 760 mmHg
• Flash Point: 247 °C
• Appearance: /
• Density: 1.213 g/cm³
• Storage Temp.: -15°C
• PKA: 3.74±0.10(Predicted)
• CAS DataBase Reference: Boc-4-Amino-L-phenylalanine(CAS DataBase Reference)
• NIST Chemistry Reference: Boc-4-Amino-L-phenylalanine(55533-24-9)
• EPA Substance Registry System: Boc-4-Amino-L-phenylalanine(55533-24-9)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-28
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 55533-24-9(Hazardous Substances Data)

Usage

Description

Boc-4-Amino-L-phenylalanine, also known as N-(tert-butoxycarbonyl)-4-amino-L-phenylalanine, is a synthetic derivative of the naturally occurring amino acid L-phenylalanine. It is characterized by the presence of a tert-butoxycarbonyl (Boc) protecting group on the amino group and a free amino group at the 4-position of the phenyl ring. Boc-4-Amino-L-phenylalanine is a white to off-white powder and is widely utilized in the field of organic chemistry and pharmaceuticals due to its unique structural features.

Uses

Used in Pharmaceutical Industry:
Boc-4-Amino-L-phenylalanine is used as an intermediate for the synthesis of biotinylated amino acids. The incorporation of biotin into amino acids enhances their affinity for specific receptors or enzymes, which can be exploited for various therapeutic applications. This modification can improve the targeting, efficacy, and pharmacokinetic properties of the resulting biotinylated compounds.
Used in Organic Chemistry:
As a protected derivative of L-phenylalanine, Boc-4-Amino-L-phenylalanine serves as a valuable building block in the synthesis of various complex organic molecules, including pharmaceuticals, agrochemicals, and other specialty chemicals. The Boc protecting group can be selectively removed under mild acidic conditions, allowing for further functionalization and modification of the molecule.
Used in Research and Development:
Boc-4-Amino-L-phenylalanine is also employed in research and development settings, where it can be used to study the effects of structural modifications on the properties and functions of amino acids and their derivatives. This knowledge can be applied to the design and development of novel bioactive molecules with improved pharmacological profiles.

Upstream product

• 33305-77-0 Boc-Phe(p-NO₂)-OH 
• 33173-55-6 (S)-3-(4-azidophenyl)-2-((tert-butoxycarbonyl)amino)propanoic acid 
• 63-91-2 L-phenylalanine 
• 949-99-5 4-nitro-3-phenyl-L-alanine 
• 24424-99-5 di-tert-butyl dicarbonate 
• 80994-44-1 {[(tert-butoxycarbonyl)oxy]amino}(phenyl)acetonitrile 
• 86937-80-6 2-tert-butoxycarbonylamino-3-(4-nitro-phenyl)-propionic acid 
• 33305-77-0 (2R)-2-{[(tert-butoxy)carbonyl]amino}-3-(4-nitrophenyl)propanoic acid 
• 673-06-3 D-(R)-phenylalanine 
• 56613-61-7 (R)-4-nitro-phenylalanine 

Downstream Products

• 114346-31-5 (S)-3-(4-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)phenyl)-2-((tert-butoxycarbonyl)amino)propanoic acid 
• 114346-31-5 (R)-3-(4-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)phenyl)-2-((tert-butoxycarbonyl)amino)propanoic acid 
• 55533-25-0 Boc-p-amino-Phe(Z)-OH 
• 98044-59-8 (S)-3-(4-Benzyloxycarbonylamino-cyclohexyl)-2-tert-butoxycarbonylamino-propionic acid 
• 106566-43-2 (S)-3-(4-Benzyloxycarbonylamino-cyclohexyl)-2-tert-butoxycarbonylamino-propionic acid 
• 33173-55-6 (S)-3-(4-azidophenyl)-2-((tert-butoxycarbonyl)amino)propanoic acid 
• 200268-13-9 {1-(4-amino-benzyl)-2-[4-(2-fluoro-ethyl)-piperidin-1-yl]-2-oxo-ethyl}-carbamic acid tert-butyl ester 
• 623563-65-5 2-{4-[3-(4-amino-phenyl)-2-tert-butoxycarbonylamino-propionylamino]-butoxy}-6-benzyloxy-benzoic acid methyl ester 
• 846569-62-8 (R)-3-(4-amino-3-iodophenyl)-2-tert-butoxycarbonylaminopropionic acid 
• 906734-92-7 (S,E)-2-((tert-butoxycarbonyl)amino)-3-(4-(phenyldiazenyl)phenyl)propanoic acid 
• 114117-42-9 N-Boc-L-p-acetylamido-phenylalanine 

Relevant articles and documents

Structure-activity relationship studies of dipeptide-based hepsin inhibitors with Arg bioisosteres

Hepsin is a type II transmembrane serine protease (TTSP) associated with cell proliferation and overexpressed in several types of cancer including prostate cancer (PCa). Because of its significant role in cancer progression and metastasis, hepsin is an attractive protein as a potential therapeutic and diagnostic biomarker for PCa. Based on the reported Leu-Arg dipeptide-based hepsin inhibitors, we performed structural modification and determined in vitro hepsin- and matriptase-inhibitory activities. Comprehensive structure-activity relationship studies identified that the p-guanidinophenylalanine-based dipeptide analog 22a exhibited a strong hepsin-inhibitory activity (Ki = 50.5 nM) and 22-fold hepsin selectivity over matriptase. Compound 22a could be a prototype molecule for structural optimization of dipeptide-based hepsin inhibitors.

Large amino acid transporter 1 (LAT1) prodrugs of valproic acid: New prodrug design ideas for central nervous system delivery

Central nervous system (CNS) drug delivery is a major challenge in drug development because the blood-brain barrier (BBB) efficiently restricts the entry of drug molecules into the CNS at sufficient amounts. The brain uptake of poorly penetrating drugs could be improved by utilizing the transporters at the BBB with a prodrug approach. In this study, we designed four phenylalanine derivatives of valproic acid and studied their ability to utilize a large amino acid transporter 1 (LAT1) in CNS delivery with an aim to show that the meta-substituted phenylalanine prodrugs bind to LAT1 with a higher affinity compared with the affinity of the para-substituted derivatives. All of the prodrugs crossed the BBB carrier mediatedly via LAT1 in in situ rat brain perfusion. For the first time, we introduced a novel meta-substituted phenylalanine analogue promoiety which improved the LAT1 affinity 10-fold and more importantly the rat brain uptake of the prodrug 2-fold compared with those of the para-substituted derivatives. Therefore, we have characterized a new prodrug design idea for CNS drug delivery utilizing a transporter-mediated prodrug approach.

Melphalan derivatives and their use as cancer chemotherapeutic drugs

The invention refers to new alkylating di- and tripeptides based on a melphalan unit, and one or two additional amino acids or amino acid derivatives, which can be used in the treatment of carcinogenic diseases. Further, the invention refers to a a pharmaceutical composition comprising the alkylating peptides of the invention.