70-78-0

Basic information

• Product Name: 3-IODO-L-TYROSINE
• Synonyms: 3-Iodo-4-hydroxyphenylalanine;4-Hydroxy-3-iodophenylalanine;3-iodine-L- tyrosine;3-I-L-Tyr-OH;3-Iodo-L-tyrosine≥ 98% (HPLC);H-L-Phe(3-I,4-OH)-OH;L-TYROSINE, 3-IODO-;H-TYR(M-I)-OH
• CAS NO: 70-78-0
• Molecular Formula: C₉H₁₀INO₃
• Molecular Weight: 307.09
• EINECS: 200-744-8
• Product Categories: amino;Unusual Amino Acids;Amino Acids 13C, 2H, 15N;Amino Acids;Biochemistry;Biological-modified Amino Acids;Amino Acids & Derivatives;Inhibitors;Aromatics;Chiral Reagents
• Mol File: 70-78-0.mol
• Article Data: 16

Chemical Properties

• Melting Point: 210 °C (dec.)(lit.)
• Boiling Point: 390.969 °C at 760 mmHg
• Flash Point: 190.251 °C
• Appearance: White to off-white/Solid
• Density: 1.7280 (estimate)
• Vapor Pressure: 8.18E-07mmHg at 25°C
• Refractive Index: 1.688
• Storage Temp.: 2-8°C
• Solubility: dilute aqueous acid: soluble
• PKA: 2.21±0.20(Predicted)
• Sensitive: Light Sensitive
• Stability: Hygroscopic
• Merck: 14,5047
• BRN: 2941266
• CAS DataBase Reference: 3-IODO-L-TYROSINE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-IODO-L-TYROSINE(70-78-0)
• EPA Substance Registry System: 3-IODO-L-TYROSINE(70-78-0)

Safety Data

• Safety Statements: 24/25
• WGK Germany: 3
• F: 8-10-23
• Hazardous Substances Data: 70-78-0(Hazardous Substances Data)

Usage

Chemical Properties

White Solid

Uses

Different sources of media describe the Uses of 70-78-0 differently. You can refer to the following data:
1. A novel flavoprotein responsible for iodide salvage in thyroid glands. A tyrosine hydroxylase inhibitor.
2. 3-iodo-l-tyrosine is used in the inhibition of tyrosine hydroxylase. 3-iodo-L-tyrosine is used in the rapid induction of prolactin secretion.
3. 3-Iodo-L-tyrosine has been used as an inhibitor for tyrosine hydroxylase enzyme in Drosophila and silkworm pupae.

Definition

ChEBI: The monoiodotyrosine that is L-tyrosine carrying an iodo-substituent at position C-3 of the benzyl group.

General Description

Iodotyrosine coupled with di-iodotyrosine results in the synthesis of 3,5,3′-tri-iodothyronine (T3) or 3,3′,5′-tri-iodothyronine (rT3).

Biochem/physiol Actions

3-iodotyrosine (3-IY) inhibits tyrosine hydroxylase that catalyzes levodopa (L-DOPA) formation from tyrosine. Iodotyrosine deiodinase enzyme deficiency leads to elevated levels of 3-IY in serum and urine in severe hypothyroidism and goiter.

Purification Methods

Likely impurities are tyrosine, diiodotyrosine and iodide. Crystallise it by dissolving it in concentrated ammonia (~200mg in ~20mL), evaporate to ~5mL and NH4Cl is added to pH4.5—5.0. After a few hours at 0o, the amino acid crystallises in needles. It is filtered off, washed with a little ice-cold H2O and dried in a vacuum. Alternatively dissolve it in dilute ammonia at room temperature, then add dilute acetic acid to pH 6. Store it at 0o. Recrystallisation of ~250mg from H2O (~5mL) removes any diiodotyrosine. It is an inhibitor of tyrosine hydroxylase with a Ki of ~500nM. [Harrington & Rivers Biochem J 38 320 1944, Rivers Chem & Ind (London) 21 1956, Beilstein 14 III 1562, 14 IV 1562.]

InChI:InChI=1/C9H10INO3/c10-6-3-5(1-2-8(6)12)4-7(11)9(13)14/h1-3,7,12H,4,11H2,(H,13,14)/t7-/m1/s1

Upstream product

• 29588-94-1 N-phthaloyl-L-tyrosine 
• 300-39-0 3,5-diiodo-l-tyrosine 
• 60-18-4 L-tyrosine 
• 79677-58-0 2-amino-3-(3-iodo-4-hydroxyphenyl)propionic acid methyl ester hydrochloride 

Downstream Products

• 315203-50-0 N-benzyloxycarbonyl-O-benzyl-L-tyrosine benzyl ester 
• 127927-74-6 (S)-2-Amino-3-(3-iodo-4-methoxymethoxy-phenyl)-propionic acid methyl ester 
• 127927-77-9 (S)-2-Amino-3-(3-{4-[(S)-2-tert-butoxycarbonylamino-2-(carboxymethyl-carbamoyl)-ethyl]-phenylsulfanyl}-4-methoxymethoxy-phenyl)-propionic acid methyl ester 
• 167550-55-2 tert-butyl 3-iodo-L-tyrosinate 
• 71400-63-0 N-tert-butyloxycarbonyl-3-iodo-L-tyrosine 
• 60-18-4 L-tyrosine 
• 130934-38-2 3-iodotyrosine phenoxyl radical 
• 79677-62-6 (S)-2-(((benzyloxy)carbonyl)amino)-3-(4-hydroxy-3-iodophenyl)propanoic acid 
• 300-39-0 3,5-diiodo-l-tyrosine 
• 70277-02-0 3-iodo-L-tyrosine methyl ester 
• 79677-58-0 2-amino-3-(3-iodo-4-hydroxyphenyl)propionic acid methyl ester hydrochloride 
• 54709-23-8 3,4-dihydroxy-5-iodo-L-phenylalanine 

Relevant articles and documents

Inhibition of thyroid peroxidase by dietary flavonoids

Flavonoids are widely distributed in plant-derived foods and possess a variety of biological activities including antithyroid effects in experimental animals and humans. A structure-activity study of 13 commonly consumed flavonoids was conducted to evaluate inhibition of thyroid peroxidase (TPO), the enzyme that catalyzes thyroid hormone biosynthesis. Most flavonoids tested were potent inhibitors of TPO, with IC50 values ranging from 0.6 to 41 μM. Inhibition by the more potent compounds, fisetin, kaempferol, naringenin, and quercetin, which contain a resorcinol moiety, was consistent with mechanism-based inactivation of TPO as previously observed for resorcinol and derivatives. Other flavonoids inhibited TPO by different mechanisms, such as myricetin and naringin, showed noncompetitive inhibition of tyrosine iodination with respect to iodine ion and linear mixed-type inhibition with respect to hydrogen peroxide. In contrast, biochanin A was found to be an alternate substrate for iodination. The major product, 6,8- diiodo-biochanin A, was characterized by electrospray mass spectrometry and 1H-NMR. These inhibitory mechanisms for flavonoids are consistent with the antithyroid effects observed in experimental animals and, further, predict differences in hazards for antithyroid effects in humans consuming dietary flavonoids. In vivo, suicide substrate inhibition, which could be reversed only by de novo protein synthesis, would be long-lasting. However, the effects of reversible binding inhibitors and alternate substrates would be temporary due to attenuation by metabolism and excretion. The central role of hormonal regulation in growth and proliferation of thyroid tissue suggests that chronic consumption of flavonoids, especially suicide substrates, could play a role in the etiology of thyroid cancer.

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.

Repurposing a Library of Human Cathepsin L Ligands: Identification of Macrocyclic Lactams as Potent Rhodesain and Trypanosoma brucei Inhibitors

Rhodesain (RD) is a parasitic, human cathepsin L (hCatL) like cysteine protease produced by Trypanosoma brucei (T. b.) species and a potential drug target for the treatment of human African trypanosomiasis (HAT). A library of hCatL inhibitors was screened, and macrocyclic lactams were identified as potent RD inhibitors (Ki 50 400 nM). SARs addressing the S2 and S3 pockets of RD were established. Three cocrystal structures with RD revealed a noncovalent binding mode of this ligand class due to oxidation of the catalytic Cys25 to a sulfenic acid (Cys-SOH) during crystallization. The P-glycoprotein efflux ratio was measured and the in vivo brain penetration in rats determined. When tested in vivo in acute HAT model, the compounds permitted up to 16.25 (vs 13.0 for untreated controls) mean days of survival.