600737-79-9

Usage

Uses

Used in Pharmaceutical Industry:
3-Iodo-N-[(benzyloxy)carbonyl]-O-benzyl-L-tyrosine Benzyl Ester is used as a reactant for the preparation of Dityrosine, Trityrosine, and Pulcherosine, which are bioactive molecules with potential applications in drug development. These molecules have been studied for their potential therapeutic effects in various diseases, including neurodegenerative disorders and cancer.
Used in Organic Synthesis:
3-Iodo-N-[(benzyloxy)carbonyl]-O-benzyl-L-tyrosine Benzyl Ester is used as a versatile building block in organic synthesis, allowing for the development of novel compounds with potential applications in various fields, such as pharmaceuticals, agrochemicals, and materials science. Its unique structure and functional groups make it a valuable intermediate for the synthesis of complex organic molecules.
Used in Medicinal Chemistry:
3-Iodo-N-[(benzyloxy)carbonyl]-O-benzyl-L-tyrosine Benzyl Ester is used as a key intermediate in the synthesis of bioactive compounds for medicinal chemistry research. Its unique structure and functional groups enable the development of new drugs and drug candidates with potential therapeutic effects in various diseases and conditions.

Upstream product

• 315203-50-0 N-benzyloxycarbonyl-O-benzyl-L-tyrosine benzyl ester 
• 501-53-1 benzyl chloroformate 
• 100-39-0 benzyl bromide 
• 79677-62-6 (S)-2-(((benzyloxy)carbonyl)amino)-3-(4-hydroxy-3-iodophenyl)propanoic acid 
• 5513-40-6 benzyl N-carbobenzyloxy-L-tyrosine 
• 70-78-0 3-Iodo-L-tyrosine 
• 213757-66-5 (S)-2-Benzyloxycarbonylamino-3-(4-hydroxy-3-iodo-phenyl)-propionic acid benzyl ester 

Downstream Products

• 765908-37-0 C₃₁H₃₀BNO₇ 
• 906356-31-8 benzyl (S)-3-(6-(benzyloxy)-[1,1'-biphenyl]-3-yl)-2-(((benzyloxy)carbonyl)amino)propanoate 
• 866115-07-3 (S)-3-{2'-Benzyloxy-5'-((S)-2-benzyloxycarbonyl-2-benzyloxycarbonylamino-ethyl)-5-[4-((S)-2-benzyloxycarbonyl-2-benzyloxycarbonylamino-ethyl)-phenoxy]-6-hydroxy-biphenyl-3-yl}-2-benzyloxycarbonylamino-propionic acid benzyl ester 
• 600737-85-7 (S)-2-Benzyloxycarbonylamino-3-[6,2'-bis-benzyloxy-5'-((S)-2-benzyloxycarbonyl-2-benzyloxycarbonylamino-ethyl)-biphenyl-3-yl]-propionic acid benzyl ester 
• 315203-50-0 N-benzyloxycarbonyl-O-benzyl-L-tyrosine benzyl ester 
• 600737-82-4 (S)-2-Benzyloxycarbonylamino-3-[4-benzyloxy-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-propionic acid benzyl ester 

Relevant academic research and scientific papers

LAT-1 activity of meta-substituted phenylalanine and tyrosine analogs

The transporter protein Large-neutral Amino Acid Transporter 1 (LAT-1, SLC7A5) is responsible for transporting amino acids such as tyrosine and phenylalanine as well as thyroid hormones, and it has been exploited as a drug delivery mechanism. Recently its role in cancer has become increasingly appreciated, as it has been found to be up-regulated in many different tumor types, and its expression levels have been correlated with prognosis. Substitution at the meta position of aromatic amino acids has been reported to increase affinity for LAT-1; however, the SAR for this position has not previously been explored. Guided by newly refined computational models of the binding site, we hypothesized that groups capable of filling a hydrophobic pocket would increase binding to LAT-1, resulting in improved substrates relative to parent amino acid. Tyrosine and phenylalanine analogs substituted at the meta position with halogens, alkyl and aryl groups were synthesized and tested in cis-inhibition and trans-stimulation cell assays to determine activity. Contrary to our initial hypothesis we found that lipophilicity was correlated with diminished substrate activity and increased inhibition of the transporter. The synthesis and SAR of meta-substituted phenylalanine and tyrosine analogs is described.

Synthesis of the side chain cross-linked tyrosine oligomers dityrosine, trityrosine, and pulcherosine

An efficient synthesis of dityrosine and the first syntheses of the tyrosine trimers trityrosine and pulcherosine have been achieved. Protected 3-iodotyrosine underwent tandem Miyaura borylation-Suzuki coupling to give protected dityrosine. The choice of

A convenient preparation of dityrosine via Miyaura borylation-Suzuki coupling of iodotyrosine derivatives

Dityrosine has been prepared from 3-iodo-L-tyrosine derivatives by sequential Miyaura borylation and Suzuki coupling reactions. A tandem borylation-coupling protocol results in improved yields of the dityrosine derivatives. Suitable protecting group strat