79677-62-6

Basic information

• Product Name: 3-Iodo-N-[(benzyloxy)carbonyl]-L-tyrosine
• Synonyms: 3-Iodo-N-[(benzyloxy)carbonyl]-L-tyrosine;RCVSCHJHQHQCGN-AWEZNQCLSA-N
• CAS NO: 79677-62-6
• Molecular Formula: C₁₇H₁₆INO₅
• Molecular Weight: 441.21711
• Product Categories: Amines, Aromatics, Pharmaceuticals, Intermediates & Fine Chemicals
• Mol File: 79677-62-6.mol
• Article Data: 9

Chemical Properties

• Appearance: /
• Solubility: Methanol
• CAS DataBase Reference: 3-Iodo-N-[(benzyloxy)carbonyl]-L-tyrosine(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Iodo-N-[(benzyloxy)carbonyl]-L-tyrosine(79677-62-6)
• EPA Substance Registry System: 3-Iodo-N-[(benzyloxy)carbonyl]-L-tyrosine(79677-62-6)

Safety Data

• Hazardous Substances Data: 79677-62-6(Hazardous Substances Data)

Usage

Description

3-Iodo-N-[(benzyloxy)carbonyl]-L-tyrosine is a synthetic organic compound that serves as a key reactant in the synthesis of various bioactive molecules. It is characterized by the presence of an iodine atom at the third position of the tyrosine molecule, which is protected by a benzyloxycarbonyl group. This unique structure makes it a valuable intermediate in the development of pharmaceutical compounds and research tools.

Uses

Used in Pharmaceutical Synthesis:
3-Iodo-N-[(benzyloxy)carbonyl]-L-tyrosine is used as a reactant in the preparation of diazonamide A, a potent anti-cancer agent. It plays a crucial role in the synthesis process, contributing to the development of this therapeutic compound.
Used in Enzyme Inhibitor Development:
In the field of biochemistry, 3-Iodo-N-[(benzyloxy)carbonyl]-L-tyrosine is utilized as a reactant for the synthesis of peptidyl and azapeptidyl Me ketones. These compounds act as substrate analog inhibitors for enzymes such as papain and cathepsin B. By inhibiting these enzymes, researchers can study their functions and develop potential therapeutic agents targeting these enzymes for various diseases.
Used in Research Applications:
3-Iodo-N-[(benzyloxy)carbonyl]-L-tyrosine is also employed as a research tool in the study of protein synthesis, enzymatic reactions, and the development of novel drug candidates. Its unique structure allows for the exploration of new chemical reactions and the design of innovative synthetic pathways, contributing to the advancement of scientific knowledge in these areas.

Upstream product

• 13139-17-8 N-(Benzyloxycarbonyloxy)succinimide 
• 70-78-0 3-Iodo-L-tyrosine 
• 60-18-4 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 
• 19506-72-0 benzyl-8-quinolyl carbonate 
• 501-53-1 benzyl chloroformate 
• 79677-60-4 (S)-N-benzyloxycarbonyl-3-(4-hydroxy-3-iodophenyl)alanine methyl ester 

Downstream Products

• 906356-31-8 benzyl (S)-3-(6-(benzyloxy)-[1,1'-biphenyl]-3-yl)-2-(((benzyloxy)carbonyl)amino)propanoate 
• 600737-79-9 benzyl (S)-3-(4-(benzyloxy)-3-iodophenyl)-2-(((benzyloxy)carbonyl)amino)propanoate 
• 150650-88-7 1-(N-benzyloxycarbonyl-3-iodo-L-tyrosyl)-2-methyl-2-tert-butoxycarbonyl hydrazine 

Relevant articles and documents

RA-XXV and RA-XXVI, Bicyclic Hexapeptides from Rubia cordifolia L.: Structure, Synthesis, and Conformation

Two RA-series bicyclic hexapeptides, RA-XXV (4) and RA-XXVI (5), which have no N-methyl group at Tyr-5, were isolated from the roots of Rubia cordifolia L. Their amino acid compositions and sequences were determined by interpretation of MS, and 1D and 2D NMR data and their relative structures were elucidated by XRD analysis of 4 and RA-XXVI acetate (6). The absolute stereochemistry of 4 was established by the total synthesis of 4, and that of 5, by the chemical correlation with 4. Peptides 4 and 5 exhibited cytotoxicity toward human promyelocytic leukemia HL-60 (IC50=0.062 and 0.066 μm, respectively) and human colonic carcinoma HCT-116 (IC50=0.028 and 0.051 μm, respectively) cell lines. Analysis of the conformational structures of 4 and 6 in the crystalline state and those of 4 and 5 in solution revealed that the N-methyl group at Tyr-5 functions to make this series of peptides preferentially adopt the active conformation.

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.

The diazo route to diazonamide A: Studies on the tyrosine-derived fragment

Various approaches to the tyrosine-derived fragment of the marine secondary metabolite diazonamide A are described. Initial efforts were focused on the originally proposed structure of the natural product, and a feasibility study established that a model