FMOC-3-NITRO-L-TYROSINE

Base Information

• Chemical Name: FMOC-3-NITRO-L-TYROSINE
• CAS No.: 136590-09-5
• Molecular Formula: C24H20N2O7
• Molecular Weight: 448.432
• Hs Code.: 29242990
• Mol file: 136590-09-5.mol

Synonyms:Fmoc-L-3-nitrotyrosine;Fmoc-3-Nitro-Tyrosine;Fmoc-Tyr(3-NO2)-OH;

Chemical Property of FMOC-3-NITRO-L-TYROSINE

Chemical Property:

• Vapor Pressure: 7.97E-21mmHg at 25°C
• Refractive Index: 1.667
• Boiling Point: 704.4 °C at 760 mmHg
• PKA: 2.77±0.10(Predicted)
• Flash Point: 379.8 °C
• PSA: 141.68000
• Density: 1.429 g/cm³
• LogP: 4.74890
• Storage Temp.: 2-8°C

Purity/Quality:

97% ^*data from raw suppliers

Fmoc-3-nitro-L-tyrosine ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

Technology Process of FMOC-3-NITRO-L-TYROSINE

There total 7 articles about FMOC-3-NITRO-L-TYROSINE which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 90.0%

3-nitro-L-tyrosine (621-44-3) + N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide (82911-69-1) → (S)-3-(3-nitro-4-hydroxyphenyl)-2-(9H-fluoren-9-ylmethoxycarbonylamino)propionic acid (136590-09-5)

Guidance literature:

With sodium carbonate; In water; acetone; at 0 - 20 ℃; for 6h; pH=9.2;

DOI:10.1007/s00726-015-2163-2

Reference yield: 80.0%

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide (82911-69-1) + L-3-(3-nitro-4-hydroxyphenyl)alanine hydrochloride → (S)-3-(3-nitro-4-hydroxyphenyl)-2-(9H-fluoren-9-ylmethoxycarbonylamino)propionic acid (136590-09-5)

Guidance literature:

With sodium carbonate; In 1,4-dioxane; at 20 ℃;

DOI:10.1021/jm050910x

Reference yield:

L-Tyr-OMe (1080-06-4) → (S)-3-(3-nitro-4-hydroxyphenyl)-2-(9H-fluoren-9-ylmethoxycarbonylamino)propionic acid (136590-09-5)

Guidance literature:

Multi-step reaction with 4 steps

1: aq. NaHCO₃

2: 85 percent / NaNO₃; HCl; La(NO₃)3

3: aq. KOH

4: aq. Na₂CO₃ / dioxane

With hydrogenchloride; potassium hydroxide; sodium nitrate; sodium hydrogencarbonate; sodium carbonate; lanthanum(III) nitrate; In 1,4-dioxane;

DOI:10.1016/j.bmcl.2004.03.103

upstream raw materials:

3-nitro-L-tyrosine

9-fluorenylmethyl N-succinimidyl carbonate

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide

L-Tyr-OMe

Downstream raw materials:

methyl N-(9-fluorenylmethoxycarbonyl)-3-nitro-L-tyrosinate

Fmoc-3-amino-L-tyrosine

Abz-RRRRAPGD-nY-NH₂

Abz-RRRRSAGM-nY-NH₂

Refernces

Design and synthesis of phosphotyrosine mimetics

10.1016/S0960-894X(03)00253-1

The research focuses on the design and synthesis of phosphotyrosine mimetics, which are of significant interest as potential therapeutic agents and research tools for selectively inhibiting protein tyrosine phosphatases (PTPases). These enzymes play a crucial role in regulating tyrosine phosphorylation and cellular function, and their inhibition could have therapeutic potential for diseases such as diabetes, cancer, and osteoporosis. The study involved the synthesis of phenylalanine derivatives, designed to mimic phosphorylated tyrosine or to act as irreversible active site inhibitors of PTPases. Key chemicals used in the synthesis process included Fmoc-l-Tyr-(3-NO2)-OH, CDI, MeOH, SnCl2, phosgene, TsCl, pyridine, SO2Cl2, and various other reagents and solvents. The synthesized compounds were then incorporated into a combinatorial library and screened for their ability to inhibit four phosphatases, showing moderate potency and selectivity, with the type 2d phosphotyrosine mimetic exhibiting the best activity. However, further analysis of enzymatic inhibition was not possible due to the termination of operations at Molecumetics.