214630-08-7

Basic information

• Product Name: BOC-3,5-DIIODO-D-TYROSINE
• Synonyms: BOC-D-TYR(3,5-12)-OH;BOC-D-TYR(3,5-I2)-OH;BOC-3,5-DIIODO-D-TYR-OH;BOC-3,5-DIIODO-D-TYROSINE;N-ALPHA-T-BUTOXYCARBONYL-3,5-DIIODO-D-TYROSINE;(R)-2-(tert-butoxycarbonylamino)-3-(4-hydroxy-3,5-diiodophenyl)propanoic acid;Boc-D-Tyr(3,5-I2)-OH Boc-3,5-Diiodo-D-tyrosine;N-[(1,1-Dimethylethoxy)carbonyl]-3,5-diiodo-D-tyrosine
• CAS NO: 214630-08-7
• Molecular Formula: C14H17I2NO5
• Molecular Weight: 533.1
• Mol File: 214630-08-7.mol

Chemical Properties

• Boiling Point: 513.3 °C at 760 mmHg
• Flash Point: 264.2 °C
• Appearance: /
• Density: 1.965 g/cm³
• Vapor Pressure: 2.32E-11mmHg at 25°C
• Refractive Index: 1.643
• Storage Temp.: -15°C
• CAS DataBase Reference: BOC-3,5-DIIODO-D-TYROSINE(CAS DataBase Reference)
• NIST Chemistry Reference: BOC-3,5-DIIODO-D-TYROSINE(214630-08-7)
• EPA Substance Registry System: BOC-3,5-DIIODO-D-TYROSINE(214630-08-7)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 214630-08-7(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical and Biochemical Research:
BOC-3,5-DIIODO-D-TYROSINE is used as a research compound for the development of new drugs and the study of protein structure and function. Its unique modification with iodine atoms and a BOC protecting group may provide specific advantages in these areas, such as enhancing the compound's stability or reactivity.
Used in Radiopharmaceuticals and Medical Imaging:
Due to its iodine-containing structure, BOC-3,5-DIIODO-D-TYROSINE is used as a potential agent in radiopharmaceuticals and medical imaging. The presence of iodine atoms allows for the compound to be utilized in imaging techniques that rely on the detection of radioactive isotopes, such as positron emission tomography (PET) or single-photon emission computed tomography (SPECT), where iodine-125 or iodine-123 can be used as radiotracers.
Used in Drug Development:
BOC-3,5-DIIODO-D-TYROSINE is used as a building block or intermediate in the synthesis of pharmaceutical compounds. Its unique properties, including the presence of iodine and the BOC protecting group, may contribute to the development of drugs with novel mechanisms of action or improved pharmacokinetic profiles.
Used in Protein Synthesis and Neurotransmitter Production Research:
As a derivative of the amino acid tyrosine, which is involved in protein synthesis and neurotransmitter production, BOC-3,5-DIIODO-D-TYROSINE is used as a research tool to study the role of tyrosine in these biological processes. The modifications to the compound may provide insights into the effects of structural changes on protein function and neurotransmitter synthesis.

InChI:InChI=1/C14H17I2NO5/c1-14(2,3)22-13(21)17-10(12(19)20)6-7-4-8(15)11(18)9(16)5-7/h4-5,10,18H,6H2,1-3H3,(H,17,21)(H,19,20)/t10-/m1/s1

Upstream product

• 60-18-4 L-tyrosine 
• 128781-80-6 (S)-methyl 2-((tert-butoxycarbonyl)amino)-3-(4-hydroxy-3,5-diiodophenyl)propanoate 
• 24424-99-5 di-tert-butyl dicarbonate 
• 300-39-0 3,5-diiodo-l-tyrosine 
• 1070-19-5 N-(tert-butyloxycarbonyl) azide 

Downstream Products

• 1423720-70-0 (S)-tert-butyl 1-(3,5-diiodo-4-methoxyphenyl)-3-hydroxypropan-2-ylcarbamate 
• 1426447-00-8 (S)-tert-butyl 1-(3,5-diiodo-4-methoxyphenyl)-3-(methoxymethoxy)propan-2-ylcarbamate 
• 1426447-03-1 C₁₇H₂₇NO₇ 
• 1426447-04-2 C₁₇H₂₇NO₆ 
• 113850-74-1 methyl (S)-2-((tert-butoxycarbonyl)amino)-3-(3,5-diiodo-4-methoxyphenyl)propanoate 

Relevant articles and documents

An efficient synthesis of l-3,4,5-trioxygenated phenylalanine compounds from l-tyrosine

A new strategy for the synthesis of l-3,4,5-trioxygenated phenylalanine derivatives from l-tyrosine is developed for the first time. The approach, featuring the transformation of aryl diiodide to bis-phenol via a one-pot procedure including lithiation, boronation, and oxidation, is highly practical. By this robust protocol, N-protected l-3,5-bis(tert-butyldimethylsilyloxy)-4- methoxy-phenylalanine and l-3,4,5-trimethoxy-phenylalanine derivatives were obtained from l-tyrosine in 9 steps with 36-40% overall yields.

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.

Characterization of thyroid hormone receptor α (TRα)-specific analogs with varying inner- and outer-ring substituents

Analogs of the TRα-specific thyromimetic CO23 were synthesized and analyzed in vitro using competitive binding and transactivation assays. Like CO23, all analogs bind to both thyroid hormone receptor subtypes with about the same affinity; however, modification of CO23 by derivatization of the 3′ position of the outer-ring or replacement of the inner-ring iodides with bromides attenuates binding. Despite lacking a preference in binding to TRα, all analogs display TRα-specificity in transactivation assays using U2OS and HeLa cells. At best, several agonists exhibit an approximately 6-12-fold preference in transactivation when tested with TRα in HeLa cells. One analog, CO24, showed in vivo TRα-specific action in a tadpole metamorphosis assay.

Synthesis and structure-function studies of melanocyte stimulating hormone analogues modified in the 2 and 4(7) positions: Comparison of activities on frog skin melanophores and melanoma adenylate cyclase

The synthesis and purification of several analogues of the melanotropins with amino acid substitutions at the tyrosine-2 and methionine-4(7) positions are reported. The compounds synthesized included [4-norleucine]-α-MSH, [7-norleucine]-β(p)-MSH, [2-3',5'