79677-58-0

Basic information

• Product Name: 3-IODO-L-TYROSINE METHYL ESTER HYDROCHLORIDE
• Synonyms: 3-IODO-L-TYROSINE METHYL ESTER HYDROCHLORIDE;L-TYROSINE, 3-IODO-, METHYL ESTER, HYDROCHLORIDE;(S)-Methyl 2-amino-3-(4-hydroxy-3-iodophenyl)propanoate hydrochloride;3-iodo- L-Tyrosine methyl ester, hydrochloride (1:1)
• CAS NO: 79677-58-0
• Molecular Formula: C₁₀H₁₂INO₃*ClH
• Molecular Weight: 357.57
• Mol File: 79677-58-0.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 3-IODO-L-TYROSINE METHYL ESTER HYDROCHLORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-IODO-L-TYROSINE METHYL ESTER HYDROCHLORIDE(79677-58-0)
• EPA Substance Registry System: 3-IODO-L-TYROSINE METHYL ESTER HYDROCHLORIDE(79677-58-0)

Safety Data

• Hazardous Substances Data: 79677-58-0(Hazardous Substances Data)

Usage

Uses

Used in Medical Research:
3-IODO-L-TYROSINE METHYL ESTER HYDROCHLORIDE is used as a research compound for its potential applications in neuroscience, aiding in the investigation of brain functions and related disorders.
Used in Pharmaceutical Synthesis:
In the pharmaceutical industry, 3-IODO-L-TYROSINE METHYL ESTER HYDROCHLORIDE is used as a precursor in the synthesis of various drugs, contributing to the development of new therapeutic agents.
Used as a Biochemical Tool:
3-IODO-L-TYROSINE METHYL ESTER HYDROCHLORIDE is utilized as a biochemical tool in the study of tyrosine metabolism, helping to elucidate the mechanisms and pathways involved in this essential metabolic process.

Upstream product

• 67-56-1 methanol 
• 3078-39-5 3-iodo-DL-tyrosine 
• 70-78-0 3-Iodo-L-tyrosine 
• 60-18-4 L-tyrosine 

Downstream Products

• 52815-35-7 2,2,3,3,4,4,4-Heptafluoro-butyric acid 4-[2-(2,2,3,3,4,4,4-heptafluoro-butyrylamino)-2-methoxycarbonyl-ethyl]-2-iodo-phenyl ester 
• 79677-65-9 Boc-Gly-Ity-OMe 
• 79677-73-9 Z-Gly-Ity-OMe 
• 119336-08-2 methyl (S)-2-((tert-butoxycarbonyl)amino)-3-(4-hydroxy-3-iodophenyl)propanoate 
• 70-78-0 3-Iodo-L-tyrosine 
• 79677-60-4 (S)-N-benzyloxycarbonyl-3-(4-hydroxy-3-iodophenyl)alanine methyl ester 
• 188594-27-6 3-iodo-L-(tyrosine)-methyl ester N-benzoylamide 
• 352010-37-8 (3-iodo-4-benzoyl-L-tyrosine) methylester N-benzoylamide 
• 602301-43-9 (S)-3-(4-Hydroxy-3-iodo-phenyl)-2-((2S,3S)-2-hydroxy-3-methyl-pentanoylamino)-propionic acid methyl ester 
• 105229-41-2 N-[(phenylmethoxy)carbonyl]-3-hydroxy-O-(phenylmethyl)-L-tyrosine methyl ester 
• 132513-32-7 3-hydroxy-O-methyl-N-<(phenylmethoxy)carbonyl>-L-tyrosine methyl ester 
• 353520-84-0 (S)-N-benzyloxycarbonyl-3-(3-iodo-4-methoxyphenyl)alanine methyl ester 
• 353520-75-9 (S)-N-benzyloxycarbonyl-3-(4-methoxy-3-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)phenyl)alanine methyl ester 
• 421556-68-5 (S)-N-benzyloxycarbonyl-3-(4-benzyloxy-3-iodophenyl)alanine methyl ester 

Relevant articles and documents

Structure-Activity Relationships of cyclo(l -Tyrosyl- l -tyrosine) Derivatives Binding to Mycobacterium tuberculosis CYP121: Iodinated Analogues Promote Shift to High-Spin Adduct

A series of analogues of cyclo(l-tyrosyl-l-tyrosine), the substrate of the Mycobacterium tuberculosis enzyme CYP121, have been synthesized and analyzed by UV-vis and electron paramagnetic resonance spectroscopy and by X-ray crystallography. The introduction of iodine substituents onto cyclo(l-tyrosyl-l-tyrosine) results in sub-μM binding affinity for the CYP121 enzyme and a complete shift to the high-spin state of the heme FeIII. The introduction of halogens that are able to interact with heme groups is thus a feasible approach to the development of next-generation, tight binding inhibitors of the CYP121 enzyme, in the search for novel antitubercular compounds.

Stereocontrolled Synthesis of Arylomycin-Based Gram-Negative Antibiotic GDC-5338

We report herein an efficient, stereocontrolled, and chromatography-free synthesis of the novel broad spectrum antibiotic GDC-5338. The route features the construction of a functionalized tripeptide backbone, a high-yielding macrocyclization via a Pd-catalyzed Suzuki-Miyaura reaction, and the late-stage elaboration of key amide bonds with minimal stereochemical erosion. Through extensive reaction development and analytical understanding, these key advancements allowed the preparation of GDC-5338 in 17 steps, 15% overall yield, >99 A % HPLC, and >99:1 dr.

PROCESS FOR MAKING ARYLOMYIN RING ANALOGS

Methods for making an arylomycin ring of formula t or salts or solvates thereof, wherein R, R1, R2, R3, R4, R5, R6, R7, R8, R9, R5, R10 and Pg1 are as defined herein.

Formal Total Synthesis of Diazonamide A by Indole Oxidative Rearrangement

A short formal total synthesis of the marine natural product diazonamide A is described. The route is based on indole oxidative rearrangement, and a number of options were investigated involving migration of tyrosine or oxazole fragments upon oxidation of open chain or macrocyclic precursors. The final route proceeds from 7-bromoindole by sequential palladium-catalysed couplings of an oxazole fragment at C-2, followed by a tyrosine fragment at C-3. With the key 2,3-disubstituted indole readily in hand, formation of a macrocyclic lactam set the stage for the crucial oxidative rearrangement to a 3,3-disubstituted oxindole. Notwithstanding the concomitant formation of the unwanted indoxyl isomer, the synthesis successfully delivered, after deprotection, the key oxindole intermediate, thereby completing a formal total synthesis of diazonamide A.

Total synthesis of mycocyclosin

The first total synthesis of mycocyclosin, a diketopiperazine natural product isolated from M. tuberculosis, is described. While direct oxidative coupling of tyrosine phenolic groups was unsuccessful, construction of the highly strained bicyclic framework was successfully accomplished through an intramolecular Miyaura-Suzuki cross-coupling to generate the biaryl linkage.

Improved protocol for indoline synthesis via palladium-catalyzed intramolecular C(sp2)-H amination

An efficient method has been developed for the synthesis of indoline compounds from picolinamide (PA)-protected β-arylethylamine substrates via palladium-catalyzed intramolecular amination of ortho-C(sp2)-H bonds. These reactions feature high efficiency, low catalyst loadings, mild operating conditions, and the use of inexpensive reagents.

Synthesis of antitumor marine alkaloid discorhabdin a oxa analogues

Dlscorhabdin A (1) exhibits a strong cytotoxic activity in vitro, but it Is difficult to synthesize and handle due to the Instability of Its highly strained N.S-acetal structure. We then designed the analogues of discorhabdin A which also have strong cyto

A convenient catalyst for aqueous and protein Suzuki-Miyaura cross-coupling

(Figure Presented) A phosphine-free palladium catalyst for aqueous Suzuki-Miyaura cross-coupling is presented. The catalyst is active enough to mediate hindered, ortho-substituted biaryl couplings but mild enough for use on peptides and proteins. The Suzuki-Miyaura couplings on protein substrates are the first to proceed in useful conversions. Notably, hydrophobic aryl and vinyl groups can be transferred to the protein surface without the aid of organic solvent since the aryl- and vinylboronic acids used in the coupling are water-soluble as borate salts. The convenience and activity of this catalyst prompts use in both general synthesis and bioconjugation.

Use of a boroxazolidone complex of 3-iodo-l-tyrosine for palladium-catalyzed cross-coupling

Complexation of 3-iodo-L-tyrosine with 9-borabicyclo[3.3.1]nonane (9-BBN) provides a convenient substrate for a palladium-catalyzed coupling reaction. The complex is stable to silica gel chromatography (hexanes/ethyl acetate), dilute triethylamine in THF, and potassium fluoride in DMF. The desired product, 3-ethynyl-L-tyrosine, was released from the complex by simply diluting its solution in methanol with chloroform. Interestingly, the complex remains stable in solutions of either methanol or chloroform individually.

Preparation of selectively protected L-dopa derivatives: Oxidation of tyrosine-3-boronates

Conversion of 3-iodo-L-tyrosine to protected tyrosine-3-boronate esters, followed by oxidation with hydrogen peroxide, provides a mild and efficient method for the preparation of selectively protected L-dopa derivatives.