142847-18-5

Basic information

• Product Name: 2-[(tert-butoxycarbonyl)amino]-3-(4-hydroxyphenyl)propanoic acid
• Synonyms: 2-[(tert-butoxycarbonyl)amino]-3-(4-hydroxyphenyl)propanoic acid;N-(tert-Butoxycarbonyl)-DL-tyrosine;(Tert-Butoxy)Carbonyl DL-Tyr-OH
• CAS NO: 142847-18-5
• Molecular Formula: C₁₄H₁₉NO₅
• Molecular Weight: 281.30436
• Mol File: 142847-18-5.mol

Chemical Properties

• Boiling Point: 484.9±40.0 °C(Predicted)
• Appearance: /
• Density: 1.238±0.06 g/cm3(Predicted)
• Storage Temp.: 2-8°C
• PKA: 2.98±0.10(Predicted)
• CAS DataBase Reference: 2-[(tert-butoxycarbonyl)amino]-3-(4-hydroxyphenyl)propanoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 2-[(tert-butoxycarbonyl)amino]-3-(4-hydroxyphenyl)propanoic acid(142847-18-5)
• EPA Substance Registry System: 2-[(tert-butoxycarbonyl)amino]-3-(4-hydroxyphenyl)propanoic acid(142847-18-5)

Safety Data

• Hazardous Substances Data: 142847-18-5(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical and Biotechnology Industries:
2-[(tert-butoxycarbonyl)amino]-3-(4-hydroxyphenyl)propanoic acid is used as a building block for the synthesis of peptides and proteins. Its Boc protecting group facilitates controlled deprotection, enabling the stepwise assembly of complex peptide structures, which is essential for the development of new drugs and therapeutic agents.
Used in Drug Discovery and Design:
In the realm of drug discovery and design, 2-[(tert-butoxycarbonyl)amino]-3-(4-hydroxyphenyl)propanoic acid serves as a valuable tool due to its hydroxyphenyl group, which can bind to specific receptors or enzymes. This feature makes it instrumental in the creation of molecules with targeted biological activities, contributing to the advancement of personalized medicine and precision therapies.

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 34081-17-9 tyrosine ethyl ester 
• 556-02-5 ?Tyr 
• 2990-25-2 tyrozine hydrochloride 
• 58632-95-4 2-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrile 
• 247088-45-5 (RS)-3-(4-benzyloxy-phenyl)-2-tert-butoxycarbonylamino-propionic acid 
• 909114-65-4 tert-butyl 4,6-dimethoxy-1,3,5-triazinyl carbonate 
• 89037-64-9 1-tert-butoxycarbonyloxybenzotriazole 

Downstream Products

• 784212-71-1 Boc-D/L-Tyr(OH)-D/L-Ala-OMe 
• 94790-24-6 (S)-methyl 2-((tert-butoxycarbonyl)amino)-3-(4-methoxyphenyl)propanoate 
• 188576-13-8 methyl 2-[(t-butoxycarbonyl)amino]-3-(4-hydroxyphenyl)propanoate 
• 7635-29-2 O-methyl tyrosine 
• 141895-35-4 2-((tert-butoxycarbonyl)amino)-3-(4-methoxyphenyl)propanoic acid 
• 876945-78-7 3-(4-(benzyloxy)phenyl)-2-((tert-butoxycarbonyl)(methyl)amino)propanoic acid 
• 876945-79-8 tert-butyl (3-(4-(benzyloxy)phenyl)-1-(methoxy(methyl)amino)-1-oxopropan-2-yl)(methyl)carbamate 
• 876945-80-1 tert-butyl (1-(4-(benzyloxy)phenyl)-4-(4-methoxyphenyl)-3-oxobutan-2-yl)(methyl)carbamate 
• 876945-81-2 5-(4-(benzyloxy)benzyl)-4-(4-methoxybenzyl)-1-methyl-1H-imidazol-2-amine 
• 110189-03-2 4-((2-amino-4-(4-methoxybenzyl)-1-methyl-1H-imidazol-5-yl)methyl)phenol 
• 110189-06-5 naamidine A 

Relevant articles and documents

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Enzymatic removal of carboxyl protecting groups. 1. Cleavage of the tert-butyl moiety

(Chemical Equation Presented) A recent discovery that a certain amino acid motif (GGG-(A)X-motif) in lipases and esterases determines their activity toward tertiary alcohols prompted us to investigate the use of these biocatalysts in the mild and selective removal of tert-butyl protecting groups in amino acid derivatives and related compounds. An esterase from Bacillus subtilis (BsubpNBE) and lipase A from Candida antarctica (CAL-A) were identified as the most active enzymes, which hydrolyzed a range of tert-butyl esters of protected amino acids (e.g., Boc-Tyr-OtBu, Z-GABA-OtBu, Fmoc-GABA-O tBu) in good to high yields and left Boc, Z, and Fmoc-protecting groups intact.

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