20866-48-2

Basic information

• Product Name: BOC-TYR(BOC)-OH
• Synonyms: N,O-DI-BOC-L-TYROSINE;N,O-DI-T-BUTOXYCARBONYL-L-TYROSINE;N,O-BIS-BOC-L-TYROSINE;N-ALPHA,O-BIS-TERT-BUTYLOXYCARBONYL-L-TYROSINE;BOC-TYROSINE(BOC)-OH;BOC-TYR(BOC)-OH;BOC-L-TYR(BOC)-OH;N-ALPHA,O-BIS-T-BUTYLOXYCARBONYL-L-TYROSINE
• CAS NO: 20866-48-2
• Molecular Formula: C₁₉H₂₇NO₇
• Molecular Weight: 381.42
• Product Categories: Amino Acids
• Mol File: 20866-48-2.mol
• Article Data: 10

Chemical Properties

• Melting Point: 94-97 °C
• Boiling Point: 528.4±50.0 °C(Predicted)
• Appearance: /
• Density: 1.183±0.06 g/cm3(Predicted)
• Storage Temp.: -15°C
• PKA: 2.92±0.10(Predicted)
• CAS DataBase Reference: BOC-TYR(BOC)-OH(CAS DataBase Reference)
• NIST Chemistry Reference: BOC-TYR(BOC)-OH(20866-48-2)
• EPA Substance Registry System: BOC-TYR(BOC)-OH(20866-48-2)

Safety Data

• Hazardous Substances Data: 20866-48-2(Hazardous Substances Data)

Usage

General Description

Boc-Tyr(Boc)-OH is a chemical compound that consists of a protected tyrosine amino acid. It is commonly used in organic synthesis and peptide chemistry as it allows for the protection of the tyrosine side chain during peptide assembly. The compound features a Boc (tert-butoxycarbonyl) group attached to the amino group of tyrosine and another Boc group attached to the hydroxyl group. This protection strategy helps to prevent unwanted reactions during the synthesis of peptides and ensures that the tyrosine residue is properly incorporated into the peptide chain. Boc-Tyr(Boc)-OH is a versatile building block for the preparation of various peptides and can be deprotected under mild acidic conditions to reveal the free tyrosine residue. Overall, Boc-Tyr(Boc)-OH is an important tool for peptide chemistry and is widely used in the synthesis of bioactive peptides and pharmaceutical compounds.

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 60-18-4 L-tyrosine 
• 3978-80-1 Boc-Tyr-OH 

Downstream Products

• 94664-21-8 quinolin-8-yl ester of N,O-di-tert-butoxycarbonyltyrosine 
• 88829-53-2 N-tert-butyloxycarbonyl-O-tert-butyloxycarbonyl-L-tyrosyl-glygylglicine 
• 2387-23-7 1,3-Dicyclohexylurea 
• 96382-72-8 H-Tyr-D-Orn[*]-Phe-Asp[*]-NH2 
• 110172-15-1 H-Tyr-Orn[*]-Phe-Asp[*]-NH₂ 
• 110116-75-1 H-Tyr-D-Asp[*]-Phe-A₂bu[*]-NH₂ 
• 106818-61-5 H-Tyr-D-Orn[*]-Phe-D-Asp[*]-NH₂ 
• 110172-16-2 H-Tyr-D-Orn[*]-D-Phe-Asp[*]-NH₂ 
• 106327-80-4 H-Tyr-D-Orn[*]-Phe(NMe)-Asp[*]-NH₂ 
• 110116-74-0 H-Tyr-D-Orn[*]-Hfe-Asp[*]-NH₂ 
• 106327-79-1 H-Tyr-D-Orn[*]-Phe(p-NO₂)-D-Asp[*]-NH₂ 
• 110116-73-9 H-Tyr-D-Orn<*>-Phg-Asp<*>-NH2 
• 88829-52-1 (S)-2-[(S)-2-(2-{2-[(S)-2-tert-Butoxycarbonylamino-3-(4-tert-butoxycarbonyloxy-phenyl)-propionylamino]-thioacetylamino}-acetylamino)-3-phenyl-propionylamino]-4-methyl-pentanoic acid methyl ester 
• 71764-12-0 (S)-2-tert-Butoxycarbonylamino-3-(4-tert-butoxycarbonyloxy-phenyl)-propionic acid pentafluorophenyl ester 

Relevant articles and documents

Sequential Intermolecular Radical Addition and Reductive Radical Cyclization of Tyrosine and Phenylalanine Derivatives with Alkenes via Photoinduced Decarboxylation: Access to Ring-Constrained γ-Amino Acids

Sequential radical addition to alkenes and reductive radical cyclization of phenylalanine and tyrosine derivatives via photoinduced decarboxylation furnished ring-constrained γ-amino acids under mild conditions. A variety of alkenes such as acrylamides and acrylic esters could be employed in the photoinduced radical cascade cyclization. The yields of the ring-constrained γ-amino acids are dependent on the electron-accepting ability and steric hindrance of the alkene used. The proposed sequential reaction can also be applied for direct tethering of dipeptides to yield unique ring-constrained tetrapeptides.

Rhamnolipid inspired lipopeptides effective in preventing adhesion and biofilm formation of Candida albicans

Rhamnolipids are biodegradable low toxic biosurfactants which exert antimicrobial and anti-biofilm properties. They have attracted much attention recently due to potential applications in areas of bioremediation, therapeutics, cosmetics and agriculture, however, the full potential of these versatile molecules is yet to be explored. Based on the facts that many naturally occurring lipopeptides are potent antimicrobials, our study aimed to explore the potential of replacing rhamnose in rhamnolipids with amino acids thus creating lipopeptides that would mimic or enhance properties of the parent molecule. This would allow not only for more economical and greener production but also, due to the availability of structurally different amino acids, facile manipulation of physico-chemical and biological properties. Our synthetic efforts produced a library of 43 lipopeptides revealing biologically more potent molecules. The structural changes significantly increased, in particular, anti-biofilm properties against Candida albicans, although surface activity of the parent molecule was almost completely abolished. Our findings show that the most active compounds are leucine derivatives of 3-hydroxy acids containing benzylic ester functionality. The SAR study demonstrated a further increase in activity with aliphatic chain elongation. The most promising lipopeptides 15, 23 and 36 at 12.5 μg/mL concentration allowed only 14.3%, 5.1% and 11.2% of biofilm formation, respectively after 24 h. These compounds inhibit biofilm formation by preventing adhesion of C. albicans to abiotic and biotic surfaces.

New precursors for direct radiosynthesis of protected derivatives of O-([18F]Fluoromethyl) tyrosine

The invention describes novel and stable precursors for the direct radiosynthesis of protected derivatives of O-([18F]Fluoromethyl) tyrosines, and methods for obtaining thoses compounds.