BOC-LYS(Z)-PNA

Base Information

• Chemical Name: BOC-LYS(Z)-PNA
• CAS No.: 51078-31-0
• Molecular Formula: C25H32N4O7
• Molecular Weight: 500.54
• Hs Code.: 2924299090
• Mol file: 51078-31-0.mol

Synonyms:N-ALPHA-T-BUTYLOXYCARBONYL-N-EPSILON-BENZYLOXYCARBONYL-L-LYSINE 4-NITROANILID;N-ALPHA-TERT-BUTYLOXYCARBONYL-N-EPSILON-BENZYLOXYCARBONYL-L-LYSINE 4-NITROANILIDE;BOC-N-EPSILON-Z-L-LYSINE 4-NITROANILIDE;BOC-LYS(Z)-PNA;BOC-LYSINE(Z)-PNA;BOC-L-LYS(Z)-PNA;N-α-Boc-N-ε-Z-L-lysine 4-nitroanilide;N-a-Boc-N-e-Z-L-lysine4-nitroanilide

Chemical Property of BOC-LYS(Z)-PNA

Chemical Property:

• Vapor Pressure: 1.04E-21mmHg at 25°C
• Refractive Index: 1.577
• Boiling Point: 739.1 °C at 760 mmHg
• Flash Point: 400.8 °C
• PSA: 151.58000
• Density: 1.246 g/cm³
• LogP: 5.90130
• Storage Temp.: -15°C

Purity/Quality:

98%Min ^*data from raw suppliers

N-a-Boc-N-epsilon-cbz-L-lysine 4-nitroanilide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Boc-L-Lys(Z)-pNA is a useful intermediate used in the preparation of amino acid nitroanilides as synthons for chromogenic peptide substrates.

Technology Process of BOC-LYS(Z)-PNA

There total 3 articles about BOC-LYS(Z)-PNA 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: 84.0%

Boc-Lys(Z)-OH (2389-45-9) + 4-nitro-aniline (100-01-6,104810-17-5) → Nα-Boc-Nε-Z-lysine p-nitroanilide (51078-31-0)

Guidance literature:

With pyridine; trichlorophosphate; at -15 ℃;

DOI:10.1016/0040-4020(95)00671-T

Reference yield: 60.0%

Boc-Lys(Z)-OH (2389-45-9) + N,N'-bis(4-nitrophenyl)phospheneimidous amide (134393-23-0) → Nα-Boc-Nε-Z-lysine p-nitroanilide (51078-31-0)

Guidance literature:

With pyridine; at 40 ℃; for 2h;

DOI:10.1246/bcsj.64.1422

Reference yield:

Boc-Lys(Z)-OH (2389-45-9) + 4-nitro-benzoic acid (62-23-7) → Nα-Boc-Nε-Z-lysine p-nitroanilide (51078-31-0)

Guidance literature:

With diphenyl phosphoryl azide; triethylamine; Yield given. Multistep reaction; 1.) 1,2-dichloroethane, room temp., 2 h, then reflux, 15 min; 2.) 1,2-dichloroethane, reflux, 4 h;

DOI:10.1248/cpb.35.2698

upstream raw materials:

Boc-Lys(Z)-OH

N,N'-bis(4-nitrophenyl)phospheneimidous amide

4-nitro-aniline

4-nitro-benzoic acid

Downstream raw materials:

N-Z-D-valyl-leucyl-N^ε-Z-lysine p-nitroanilide

D-valyl-leucyl-lysine p-nitroanilide dihydrobromide

[(S)-5-{[4-(Benzyloxycarbonylamino-methyl)-cyclohexanecarbonyl]-amino}-5-(4-nitro-phenylcarbamoyl)-pentyl]-carbamic acid benzyl ester

Suc-Tyr-Leu-Lys-pNA acetate

Refernces

• 1、 Oyamada, Hidekazu,Saito, Takashi,Inaba, Shinsaku,Ueki, Masaaki. "Reinvestigation of the Phosphazo Method and Synthesis of N-(t-Butoxycarbonyl)-L-arginine p-Nitroanilide and a Chromogenic Enzyme Substrate for the Factor Xa". . p. 1422 - 1424. Retrieved 2007/10/02.
• 2、 Shioiri,Murata,Hamada. "New methods and reagents in organic synthesis. 69. A new synthesis of alpha-amino acid and peptide amides of aromatic amines using a modified Curtius reaction with diphenyl phosphorazidate.". . p. 2698 - 2704. Retrieved 2007/10/02.