5575-03-1

Basic information

• Product Name: BOC-3-NITRO-L-TYROSINE
• Synonyms: BOC-TYR(3-NO2)-OH;BOC-M-NITRO-TYR-OH;BOC-L-TYR(3-NO2);BOC-3-NITRO-L-TYROSINE;BOC-3-NITRO-TYR-OH;N-ALPHA-T-BUTOXYCARBONYL-L-(3-NITRO)TYROSINE;Boc-m-nitro-L-Tyr-OH
• CAS NO: 5575-03-1
• Molecular Formula: C₁₄H₁₈N₂O₇
• Molecular Weight: 326.3
• Mol File: 5575-03-1.mol
• Article Data: 10

Chemical Properties

• Boiling Point: 523.8±50.0 °C(Predicted)
• Appearance: /
• Density: 1.365±0.06 g/cm3(Predicted)
• Storage Temp.: Store at 0-5°C
• PKA: 2.80±0.10(Predicted)
• CAS DataBase Reference: BOC-3-NITRO-L-TYROSINE(CAS DataBase Reference)
• NIST Chemistry Reference: BOC-3-NITRO-L-TYROSINE(5575-03-1)
• EPA Substance Registry System: BOC-3-NITRO-L-TYROSINE(5575-03-1)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 5575-03-1(Hazardous Substances Data)

Usage

General Description

BOC-3-NITRO-L-TYROSINE is a chemical compound that consists of a tyrosine amino acid with a 3-nitrobenzyl carbamate group (BOC) attached to the amino group. BOC-3-NITRO-L-TYROSINE is commonly used in peptide synthesis as a protecting group for the tyrosine residue, allowing for selective deprotection and modification of other functional groups within a peptide chain. BOC-3-NITRO-L-TYROSINE is also known to exhibit nitric oxide-like effects, and has potential applications in the study of nitrotyrosine-related reactions and oxidative stress in biological systems. Additionally, it may be used as a precursor in the synthesis of pharmaceuticals and other biologically active compounds.

Upstream product

• 3978-80-1 Boc-Tyr-OH 
• 24424-99-5 di-tert-butyl dicarbonate 
• 3604-79-3 3-nitrotyrosine 
• 621-44-3 3-nitro-L-tyrosine 
• 1027739-35-0 Nitro tyrosine 

Downstream Products

• 128404-23-9 N^α-tert-butyloxycarbonyl-3-nitro-L-tyrosyl-L-proline methyl ester 
• 1253795-15-1 (S)-methyl 2-(tert-butoxycarbonylamino)-3-(4-hydroxy-3-iodo-5-nitrophenyl)propanoate 
• 1253795-07-1 (S)-2-(tert-butoxycarbonylamino)-3-(4-hydroxy-3-iodo-5-nitrophenyl)propanoic acid 
• 1305317-52-5 C₃₅H₄₈BIN₄O₁₂ 
• 154733-74-1 methyl 2-((tert-butoxycarbonyl)amino)-3-(4-methoxy-3-nitrophenyl)propanoate 
• 849191-03-3 3-(3-amino-4-methoxyphenyl)-2-(tert-butoxycarbonylamino)propionic acid methyl ester 
• 1352201-97-8 (2S)-2-amino-3-(4-hydroxy-3-nitrophenyl)-1-(1,2-oxazinan-2-yl)propan-1-one, trifluoroacetic acid salt 
• 1305317-57-0 C₅₆H₇₉N₇O₁₃ 
• 1305317-48-9 C₁₁H₁₃IN₂O₅ 
• 1253795-12-8 (S)-methyl 2-(tert-butoxycarbonylamino)-3-(3-iodo-4-methoxy-5-nitrophenyl)propanoate 
• 128404-28-4 3-nitro-L-tyrosyl-L-proline methyl ester hydrochloride 
• 125034-08-4 Cyclo-3-nitro-L-tyrosyl-L-proline 
• 129048-75-5 <3'-NO2Tyr¹>DPDPE 
• 862191-19-3 N-(tert-butoxycarbonyl)-3-aminotyrosine 

Relevant articles and documents

Plasminogen activator inhibitor-1 inhibitors and methods of use thereof to modulate lipid metabolism

The invention relates to plasminogen activator-1 (PAI-1) inhibitor compounds and uses thereof in the treatment of any disease or condition associated with elevated PAI-1. The invention includes, but is not limited to, the use of such compounds to modulate lipid metabolism and treat conditions associated with elevated PAI-1, cholesterol, or lipid levels.

Quantitative insight into the design of compounds recognized by the L-type amino acid transporter 1 (LAT1)

L-Type amino acid transporter 1 (LAT1) is a transmembrane protein expressed abundantly at the blood-brain barrier (BBB), where it ensures the transport of hydrophobic acids from the blood to the brain. Due to its unique substrate specificity and high expression at the BBB, LAT1 is an intriguing target for carrier- mediated transport of drugs into the brain. In this study, a comparative molecular field analysis (CoMFA) model with considerable statistical quality (Q2=0.53, R2=0.75, Q2 SE=0.77, R2 SE=0.57) and good external predictivity (CCC=0.91) was generated. The model was used to guide the synthesis of eight new prodrugs whose affinity for LAT1 was tested by using an in situ rat brain perfusion technique. This resulted in the creation of a novel LAT1 prodrug with l-tryptophan as the promoiety; it also provided a better understanding of the molecular features of LAT1-targeted high-affinity prodrugs, as well as their promoiety and parent drug. The results obtained will be beneficial in the rational design of novel LAT1-binding prodrugs and other compounds that bind to LAT1.

Intramolecular suzuki-miyaura reaction for the total synthesis of signal peptidase inhibitors, arylomycins A2and B2

Development of the total syntheses of arylomycins A1 and B 2 is detailed. Key features of our approach include 1) formation of 14-membered meta, meta-cyclophane by an intramolecular Suzuki-Miyaura reaction; 2) incorporation of N-Me-4-hydroxyphenylglycine into the cyclization precursor, which avoids the late-stage low-yielding N-methylation step; 3) segment coupling of a fully elaborated peptide side chain to the macrocycle, which makes the synthesis highly convergent. Overall, arylomycin A2 was obtained in 13 steps from L-Tyr for the longest linear sequence, in 13% overall yield. Arylomycin B2 was synthesized in 10 steps from L-3-nitro-Tyr, in 10% overall yield.