Ac-YVAD-AMC

Base Information

• Chemical Name: Ac-YVAD-AMC
• CAS No.: 149231-65-2
• Molecular Formula: C33H39 N5 O10
• Molecular Weight: 665.7
• DSSTox Substance ID: DTXSID20274428
• Mol file: 149231-65-2.mol

Synonyms:Ac-YVAD-AMC;Ac-Tyr-Val-Ala-Asp-AMC;DTXSID20274428;FT-0643429;N-Acetyl-Tyr-Val-Ala-Asp-7-amido-4-methylcoumarin;N-Acetyl-Tyr-Val-Ala-Asp-7-amido-4-methylcoumarin, >=99% (TLC), powder

Chemical Property of Ac-YVAD-AMC

Chemical Property:

• Appearance/Colour: white powder
• Boiling Point: 1127.3 °C at 760 mmHg
• Flash Point: 635.6 °C
• PSA: 233.24000
• Density: 1.344 g/cm³
• LogP: 2.73450
• Storage Temp.: −20°C
• Solubility.: DMSO: 10 mM The solution is stable in the dark at −20
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 7
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 14
• Exact Mass: 665.26969246
• Heavy Atom Count: 48
• Complexity: 1260

Purity/Quality:

98%,99%, ^*data from raw suppliers

N-Acetyl-Tyr-Val-Ala-Asp-7-amido-4-methylcoumarin ≥99% (TLC), powder ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC(=O)OC2=C1C=CC(=C2)NC(=O)C(CC(=O)O)NC(=O)C(C)NC(=O)C(C(C)C)NC(=O)C(CC3=CC=C(C=C3)O)NC(=O)C

Technology Process of Ac-YVAD-AMC

There total 2 articles about Ac-YVAD-AMC 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: 89.3%

Ac-Tyr(OBzl)-Val-Ala-Asp(OBzl)-MCA → acetyl-YVAD-aminomethyl coumarine (149231-65-2)

Guidance literature:

With hydrogen; palladium on activated charcoal; In methanol;

DOI:10.1248/cpb.43.1336

Reference yield:

7-amino-4-methylcoumarin. (26093-31-2) + N-Fmoc-Tyr-OH (112883-29-1,92954-90-0) + chloroformic acid ethyl ester (541-41-3) + (S)-3-(((9H-fluoren-9-yl)methoxy)carbonylamino)-4-(allyloxy)-4-oxobutanoic acid (144120-53-6) → acetyl-YVAD-aminomethyl coumarine (149231-65-2)

Guidance literature:

With piperidine; 4-methyl-morpholine; 1-methyl-pyrrolidin-2-one; dmap; tetrakis(triphenylphosphine) palladium⁽⁰⁾; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; N-methylaniline; Wang resin; Multistep reaction; solid phase synthesis;

DOI:10.1016/S0960-894X(99)00260-7

Reference yield:

acetyl-YVAD-aminomethyl coumarine (149231-65-2) → 7-amino-4-methylcoumarin. (26093-31-2)

Guidance literature:

With recombinant human caspase-1; In dimethyl sulfoxide; at 20 ℃; pH=7.4; Enzyme kinetics;

DOI:10.1021/ja0637649

upstream raw materials:

7-amino-4-methylcoumarin.

N-Fmoc-Tyr-OH

chloroformic acid ethyl ester

(S)-3-(((9H-fluoren-9-yl)methoxy)carbonylamino)-4-(allyloxy)-4-oxobutanoic acid

Downstream raw materials:

7-amino-4-methylcoumarin.

Refernces

• 1、 Taguchi,Hirano,Yokoi,Asada,Okada. "Amino acids and peptides. XL. Synthesis of Ac-Tyr-Val-Ala-Asp-MCA using newly developed acetylating reagent". . p. 1336 - 1339. Retrieved 2007/10/02.