A 54556A

Base Information

• Chemical Name: A 54556A
• CAS No.: 95398-45-1
• Molecular Formula: C₃₈H₅₀N₆O₈
• Molecular Weight: 718.85
• Mol file: 95398-45-1.mol

Synonyms:

Chemical Property of A 54556A

Chemical Property:

• Melting Point: >180oC (dec.)
• Storage Temp.: Amber Vial, Refrigerator
• Solubility.: Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)

Purity/Quality:

99% ^*data from raw suppliers

A54556A(~90%) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Description: A-54556A is an acyldepsipeptide (ADEP) antibiotic that has been found in Streptomyces hawaiiensis. It is active against B. subtilis, S. pyogenes, and E. faecalis, as well as penicillin-resistant S. pneumoniae, vancomycin-resistant E. faecium, and methicillin-resistant S. aureus (MRSA; IC50s = 0.2, 0.4, 0.4, 1.6, 0.4, and 6.3 μg/ml, respectively). It binds to and activates caseinolytic protease P (ClpP), inducing degradation of β-casein by the B. subtilis ClpP in an ATPase-independent manner when used at concentrations of 2.5 and 5 μg/ml.
• Uses: A 54556A is an unusual depsipeptide isolated from Streptomyces hawaiiensis by researchers at Eli Lilly in 1985, featuring a trienone side chain. A 54556A is potently active against Gram positive and Gram negative bacteria, including MRSA. A 54556A was the original lead structure of the recently re-discovered acyldepsipeptide (ADEP) antibiotics that act by activating and disregulating Clp-family proteins. ADEPs are considered important leads in the development of new generations of antibiotics against resistant bacteria.

Technology Process of A 54556A

There total 11 articles about A 54556A 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: 92.0%

C30H42N6O7 + (2E,4E,6E)-octa-2,4,6-trienoic acid (97329-94-7) → acyldepsipeptide 1 (95398-45-1)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; ((3H-[1,2,3]triazolo[4,5-b]pyridin-3-yl)oxy)tri(pyrrolidin-1-yl)phosphonium hexafluorophosphate(V); In dichloromethane; at 0 - 20 ℃; for 19h; Inert atmosphere; Darkness;

DOI:10.1021/np500158q

Reference yield: 51.0%

C30H42N6O7*C2HF3O2 + (2E,4E,6E)-octa-2,4,6-trienoic acid (97329-94-7) → acyldepsipeptide 1 (95398-45-1)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; ((3H-[1,2,3]triazolo[4,5-b]pyridin-3-yl)oxy)tri(pyrrolidin-1-yl)phosphonium hexafluorophosphate(V); In dichloromethane; at 0 - 20 ℃; for 48h; Inert atmosphere;

DOI:10.1021/np500158q

Reference yield:

C29H39N5O8 → acyldepsipeptide 1 (95398-45-1)

Guidance literature:

Multi-step reaction with 4 steps

1: hydrogenchloride; palladium 10% on activated carbon; hydrogen; water / methanol / 24 h / 760.05 Torr

2: N-ethyl-N,N-diisopropylamine; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate / chloroform / 36 h / 0 - 20 °C / Inert atmosphere

3: dichloromethane / 18 h / 0 - 20 °C / Inert atmosphere

4: N-ethyl-N,N-diisopropylamine; ((3H-[1,2,3]triazolo[4,5-b]pyridin-3-yl)oxy)tri(pyrrolidin-1-yl)phosphonium hexafluorophosphate(V) / dichloromethane / 48 h / 0 - 20 °C / Inert atmosphere

With hydrogenchloride; palladium 10% on activated carbon; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; water; hydrogen; N-ethyl-N,N-diisopropylamine; ((3H-[1,2,3]triazolo[4,5-b]pyridin-3-yl)oxy)tri(pyrrolidin-1-yl)phosphonium hexafluorophosphate(V); In methanol; dichloromethane; chloroform;

DOI:10.1021/np500158q

upstream raw materials:

C₁₇H₂₉N₃O₆

(2E,4E,6E)-octa-2,4,6-trienoic acid

Refernces