ALA-ALA-PRO-VAL-CMK

Base Information

• Chemical Name: ALA-ALA-PRO-VAL-CMK
• CAS No.: 90105-47-8
• Molecular Formula: C₁₇H₂₉ClN₄O₄
• Molecular Weight: 388.895
• Mol file: 90105-47-8.mol

Synonyms:ALA-ALA-PRO-VAL-CHLOROMETHYLKETONE;ALA-ALA-PRO-VAL-CMK;H-ALA-ALA-PRO-VAL-CHLOROMETHYLKETONE;H-ALA-ALA-PRO-VAL-CMK

Chemical Property of ALA-ALA-PRO-VAL-CMK

Chemical Property:

• PSA: 121.60000
• LogP: 1.19800
• Storage Temp.: -15°C
• Solubility.: Soluble in DMSO or DMF.

Purity/Quality:

98%Min ^*data from raw suppliers

H-Ala-Ala-Pro-Val-chloromethylketone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: An irreversible and cell permeable inhibitor of human leukocyte elastase. Chloromethyl ketones covalently bond to the OH of an adjacent serine residue, or to the SH of an adjacent cysteine residue, on the target protein.

Technology Process of ALA-ALA-PRO-VAL-CMK

There total 11 articles about ALA-ALA-PRO-VAL-CMK 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:

N-benzyloxycarbonyl-L-alanyl-L-proline (21027-01-0) → (S)-1-[(S)-2-((S)-2-Amino-propionylamino)-propionyl]-pyrrolidine-2-carboxylic acid ((S)-3-chloro-1-isopropyl-2-oxo-propyl)-amide (90105-47-8)

Guidance literature:

Multi-step reaction with 4 steps

1: hydrogene / Pd-C / aq. NaOH

2: dioxane / 24 h

3: 72 percent / N-ethylmorpholine, isobutyl chloroformate / tetrahydrofuran / -15 - 20 °C

4: 6.2N HCl / dioxane / 1 h

With N-ethylmorpholine;; hydrogenchloride; hydrogen; isobutyl chloroformate; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; sodium hydroxide;

Reference yield:

valyl-chloromethylketone (51370-20-8) → (S)-1-[(S)-2-((S)-2-Amino-propionylamino)-propionyl]-pyrrolidine-2-carboxylic acid ((S)-3-chloro-1-isopropyl-2-oxo-propyl)-amide (90105-47-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 72 percent / N-ethylmorpholine, isobutyl chloroformate / tetrahydrofuran / -15 - 20 °C

2: 6.2N HCl / dioxane / 1 h

With N-ethylmorpholine;; hydrogenchloride; isobutyl chloroformate; In tetrahydrofuran; 1,4-dioxane;

Reference yield:

(S)-1-chloro-3-(benzyloxycarbonylamino)-4-methyl-2-pentanone (90105-41-2) → (S)-1-[(S)-2-((S)-2-Amino-propionylamino)-propionyl]-pyrrolidine-2-carboxylic acid ((S)-3-chloro-1-isopropyl-2-oxo-propyl)-amide (90105-47-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) 5.6N HBr/AcOH, 2.) N-ethyl-morpholine / 1.) 5min, 2.) DMF

2: 72 percent / N-ethylmorpholine, isobutyl chloroformate / tetrahydrofuran / -15 - 20 °C

3: 6.2N HCl / dioxane / 1 h

With N-ethylmorpholine;; hydrogenchloride; hydrogen bromide; acetic acid; isobutyl chloroformate; In tetrahydrofuran; 1,4-dioxane;

upstream raw materials:

benzyloxycarbonyl-L-alanyl-L-alanine

L-alanyl-L-proline

N-tert-butyloxycarbonyl-alanyl-alanyl-proline

N-benzyloxycarbonyl-L-alanyl-L-proline

Downstream raw materials:

N-3-carboxypropanoyl-alanyl-alanyl-prolyl-valyl-chloromethylketone

Refernces