72155-46-5

Basic information

• Product Name: (3S,4S)-4-T-BUTYLOXYCARBONYLAMINO-3-HYDROXY-5-PHENYL-PENTANOIC ACID
• Synonyms: (3S,4S)-4-T-BUTYLOXYCARBONYLAMINO-3-HYDROXY-5-PHENYL-PENTANOIC ACID;NALPHA-tert-Butoxycarbonyl-(3S,4S)-4-amino-3-hydroxy-5-phenylpentanoic acid
• CAS NO: 72155-46-5
• Molecular Formula: C₁₈H₂₇NO₅
• Molecular Weight: 309.35752
• Product Categories: Amino Acids
• Mol File: 72155-46-5.mol
• Article Data: 20

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (3S,4S)-4-T-BUTYLOXYCARBONYLAMINO-3-HYDROXY-5-PHENYL-PENTANOIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: (3S,4S)-4-T-BUTYLOXYCARBONYLAMINO-3-HYDROXY-5-PHENYL-PENTANOIC ACID(72155-46-5)
• EPA Substance Registry System: (3S,4S)-4-T-BUTYLOXYCARBONYLAMINO-3-HYDROXY-5-PHENYL-PENTANOIC ACID(72155-46-5)

Safety Data

• Hazardous Substances Data: 72155-46-5(Hazardous Substances Data)

Usage

Description

(3S,4S)-4-T-BUTYLOXYCARBONYLAMINO-3-HYDROXY-5-PHENYL-PENTANOIC ACID, also known as Boc-phenylalanine, is a chemical compound that features a pentanoic acid backbone with a phenyl group and an amino acid functional group. The "Boc" in its name signifies the presence of a tert-butoxycarbonyl protecting group, which is crucial for preventing unwanted reactions during peptide synthesis. (3S,4S)-4-T-BUTYLOXYCARBONYLAMINO-3-HYDROXY-5-PHENYL-PENTANOIC ACID is widely recognized for its role as a building block in the synthesis of complex organic molecules and its applications in the pharmaceutical and biotechnology sectors.

Uses

Used in Pharmaceutical Industry:
Boc-phenylalanine serves as a key component in the synthesis of various drugs and research compounds. Its role in creating complex organic molecules makes it invaluable for the development of new pharmaceuticals and therapeutic agents.
Used in Biotechnology Industry:
In the biotechnology field, Boc-phenylalanine is utilized for the production of peptides and other biomolecules. Its presence as a building block allows for the creation of a wide range of biologically active compounds, contributing to advancements in research and medicine.
Used in Peptide Synthesis:
Boc-phenylalanine is employed as a crucial building block in peptide synthesis. The Boc protecting group ensures that the amino acid functional group remains intact and unreacted until the desired peptide sequence is achieved, which is essential for the successful synthesis of target peptides.
Used as a Research Compound:
In research settings, Boc-phenylalanine is often used to study the properties and interactions of amino acids and peptides. Its unique structure and functional groups make it a valuable tool for understanding the fundamentals of peptide chemistry and biology.

Upstream product

• 112271-08-6 (4S)-40<(tertibutyloxycarbonyl)amino>-3-oxo-5-phenylpentanoic acid ethyl ester 
• 58521-44-1 (4S)-4-<(tert-butyloxycarbonyl)amino>-6-methyl-3-oxoheptanoic acid ethyl ester 
• 72155-45-4 Boc-L-phenylalaninal 
• 141-78-6 ethyl acetate 
• 64-17-5 ethanol 
• 172034-33-2 [(S)-1-((R)-3,3-Dichloro-4-oxo-oxetan-2-yl)-2-phenyl-ethyl]-carbamic acid tert-butyl ester 
• 24424-99-5 di-tert-butyl dicarbonate 
• 236747-30-1 4-(tert-butoxycarbonyl-methyl-amino)-3-oxo-5-phenyl-pentanoic acid ethyl ester 
• 13734-34-4 N-tert-butoxycarbonyl-L-phenylalanine 
• 1161-13-3 N-Cbz-L-Phe 
• 55740-07-3 (4S)-4-benzyl-5-oxo-1,3-oxazolidine-3-carboxylic acid benzyl ester 
• 220931-41-9 (S)-4-Benzyl-5-[1-ethoxycarbonyl-meth-(E)-ylidene]-oxazolidine-3-carboxylic acid benzyl ester 
• 142955-51-9 N-butoxycarbonyl-L-phenylalanine anhydride 
• 51987-73-6 (S)-2-tert-butoxycarbonylamino-3-phenyl-propionic acid methyl ester 

Downstream Products

• 120742-17-8 ethyl (3S,4S)-3-hydroxy-4-amino-5-phenylpentanoate hydrochloride 
• 684643-49-0 H-(SS)-AHPPA-OEt 
• 479664-01-2 Boc-(SS)-Sta-(SS)-AHPPA-OEt 
• 72155-50-1 (3S,4S)-4-amino-3-hydroxy-5-phenylpentanoic acid 
• 172912-04-8 BocAHPPA-Phe-Leu-Phe 
• 172912-03-7 BocAHPPA-Phe-Leu-Phe-OCH₃ 
• 172912-08-2 cis-2-(tert-butyldiphenylsilyloxymethyl)-5-4-(Boc-AHPPA-1-oxo-6-aminopentyl)cytosin-1'-yl>-1,3-oxathiolane 
• 120742-12-3 N-Isovaleryl-L-valyl-L-valyl-4(S)-amino-3(S)-hydroxy-5-phenylpentanoic Acid Methyl Ester 
• 72155-66-9 N-(tert-butoxycarbonyl)-4(S)-amino-3(S)-hydroxy-5-phenylpentanoyl-L-alanyl isoamylamide 
• 72155-54-5 2-oxazolidinone of 4(S)-amino-3(S)-hydroxy-5-phenylpentanoic acid 
• 124278-65-5 (S,S)-γ-amino-β-hydroxy-N-<2-(4-morpholinyl)ethyl>cyclohexane pentanamide 
• 98105-45-4 (3S,4S)-4-(N-tert-butoxycarbonyl)amino-5-cyclohexyl-3-hydroxypentanoic acid 
• 124278-64-4 (3S,4S)-4-(N-tert-butoxycarbonyl)amino-5-cyclohexyl-3-hydroxy-N-(2-morpholinoethyl)pentanamide 
• 119357-93-6 (3S,4S)-4-((S)-2-Amino-3-thiazol-4-yl-propionylamino)-5-cyclohexyl-3-hydroxy-pentanoic acid (2-morpholin-4-yl-ethyl)-amide 

Relevant articles and documents

AHPPA derivative and its preparation method

The invention discloses AHPPA derivatives and a preparation method thereof. The preparation method utilizes a diethylzinc-stannic chloride mixture with a mole ratio of 1: 2-4 as a catalyst, improves a reaction temperature and a yield and is suitable for industrial production.

Novel renin inhibitors containing derivatives of N-alkylleucyl-β-hydroxy-γ-amino acids

In search for new drugs lowering arterial blood pressure, which could be applied in anti-hypertensive therapy, research concerning agents blocking of renin-angiotensin-aldosteron system has been conducted. Despite many years of research conducted at many research centers around the world, aliskiren is the only one renin inhibitor, which is used up to now. Four novel potential renin inhibitors, having structure based on the peptide fragment 8-13 of human angiotensinogen, a natural substrate for renin, were designed and synthesized. All these inhibitors contain unnatural moieties that are derivatives of N-methylleucyl-β-hydroxy-γ-amino acids at the P2-P1' position: 4-[N-(N-methylleucyl)-amino]-3-hydroxy-7-(3-nitroguanidino)-heptanoic acid (AHGHA), 4-[N-(N-methylleucyl)-amino]-3-hydroxy-5-phenyl-pentanoic acid (AHPPA) or 4-[N-(N-methylleucyl)-amino]-8-benzyloxycarbonylamino-3-hydroxyoctanoic acid (AAHOA). The previously listed synthetic β-hydroxy-γ-amino acids constitute pseudodipeptidic units that correspond to the P1-P1' position of the inhibitor molecule. An unnatural amino acid, 4-methoxyphenylalanin (Phe(4-OMe)), was introduced at the P3 position of the obtained compounds. Three of these compounds contain isoamylamide of 6-aminohexanoic acid (ε-Ahx-Iaa) at the P2'-P3' position. The proposed modifications of the selected human angiotensinogen fragment are intended to increase bioactivity, bioavailability, and stability of the inhibitor molecule in body fluids and tissues. The inhibitor Boc-Phe(4-OMe)-MeLeu-AHGHA-OEt was obtained in the form of an ethyl ester. The hydrophobicity coefficient, expressed as log P varied between 3.95 and 8.17. In vitro renin inhibitory activity of all obtained compounds was contained within the range 10-6-10-9 M. The compound Boc-Phe(4-OMe)-MeLeu-AHPPA-Ahx-Iaa proved to be the most active (IC50 = 1.05 × 10-9 M). The compounds Boc-Phe(4-OMe)-MeLeu-AHGHA-Ahx-Iaa and Boc-Phe(4-OMe)-MeLeu-AHPPA-Ahx-Iaa are resistant to chymotrypsin.

Stereoselective synthesis of four possible isomers of streptopyrrolidine

The synthesis of (4R,5R)-streptopyrrolidine (1), (4S,5R)-streptopyrrolidine (2) (4R, 5S)-streptopyrrolidine (3) and (4S,5S)-strepto- pyrrolidine (4) have been achieved in a concise and highly efficient manner via a highly stereoselective aldol type reacti