Bafilomycin A

Base Information

• Chemical Name: Bafilomycin A
• CAS No.: 88899-55-2
• Molecular Formula: C35H58 O9
• Molecular Weight: 622.8296
• Hs Code.: 29419090
• European Community (EC) Number: 621-324-4
• DSSTox Substance ID: DTXSID201015547
• Wikipedia: Bafilomycin
• Mol file: 88899-55-2.mol

Synonyms:bafilomycin A

Chemical Property of Bafilomycin A

Chemical Property:

• Vapor Pressure: 2.19E-27mmHg at 25°C
• Refractive Index: 1.534
• Boiling Point: 770.1 °C at 760 mmHg
• PKA: 12.66±0.70(Predicted)
• Flash Point: 232.2 °C
• PSA: 134.91000
• Density: 1.12 g/cm³
• LogP: 4.69270
• Storage Temp.: 2-8°C
• Solubility.: Soluble in DMSO (up to 5 mg/ml, with warming).
• Water Solubility.: Soluble in methanol, ethanol, acetone and chloroform. Insoluble in water.
• XLogP3: 6
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 7
• Exact Mass: 622.40808342
• Heavy Atom Count: 44
• Complexity: 1060

Purity/Quality:

96% 1H NMR ^*data from raw suppliers

Bafilomycin A1 ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC1CC(=CC=CC(C(OC(=O)C(=CC(=CC(C1O)C)C)OC)C(C)C(C(C)C2(CC(C(C(O2)C(C)C)C)O)O)O)OC)C
• Isomeric SMILES: C[C@@H]1C/C(=C/C=C/[C@@H]([C@H](OC(=O)/C(=C/C(=C/[C@H]([C@H]1O)C)/C)/OC)[C@@H](C)[C@H]([C@H](C)[C@]2(C[C@H]([C@@H]([C@H](O2)C(C)C)C)O)O)O)OC)/C
• Description: Bafilomycin A1 is a fungal metabolite that has been found in Streptomyces and has diverse biological activities. It is an inhibitor of vacuolar H+-ATPases (V-ATPases; Ki = 0.5 nM in N. crassa vacuolar membranes) and is greater than 1,000-fold selective for V-ATPases over Na+/K+-, Ca2+-, and H+-ATPases. Bafilomycin A1 (100 nM) inhibits autophagosome maturation and protein degradation in H-4-II-E cells. It inhibits chloroquine-induced apoptosis in primary cerebellar granule neurons (CGNs) but not chloroquine-induced inhibition of macroautophagy. Bafilomycin A1 (100 nM) reduces viral yield in the culture supernatant of Vero E6 and Huh7 cells, as well as HEK293T cells expressing human angiotensin-converting enzyme 2 (ACE2), infected with severe acute respiratory syndrome coronavirus 2 (SARS-CoV-2). It also reduces lung RNA copy numbers and viral pneumonia in ACE2 transgenic mice infected with SARS-CoV-2 when administered at a dose of 0.1 mg/kg.
• Uses: Bafilomycin A1 is a member of a potent family of macrocyclic lactones with broad spectrum biological activity, including activity against bacteria, yeast, fungi, nematodes, insects and tumour cell lines. Bafilomycin A1 is an inhibitor of vacuolar-type ATPase. A macrolide antibiotic and potent and selective inhibitor of vacuolar-type (v-type) H+ ATPase Bafilomycin A1 is a specific potent inhibitor of vacuolar ATPases.It is used as an antibacterial, antifungal, antineoplastic and an immunosuppressive. It prevents maturation of autophagic vacuoles by inhibiting fusion between autophagosomes and lysosomes and is a macrolide antibiotic and potent and selective inhibitor of vacuolar-type H+ ATPase (V-ATPase).

Technology Process of Bafilomycin A

There total 119 articles about Bafilomycin A 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: 94.0%

C46H82O9Si2 → bafilomycin A1 (88899-55-2)

Guidance literature:

With pyridine hydrogenfluoride; In tetrahydrofuran; at 25 ℃;

DOI:10.1016/S0040-4039(00)91817-3

Reference yield: 93.0%

(3Z,5E,11E,13E)-(7R,8S,9S,15S,16R)-16-[(1R,2R,3S,5R,6R)-2,6-Bis-(tert-butyl-dimethyl-silanyloxy)-1,3,5,7-tetramethyl-4-oxo-octyl]-3,15-dimethoxy-5,7,9,11-tetramethyl-8-triethylsilanyloxy-oxacyclohexadeca-3,5,11,13-tetraen-2-one → bafilomycin A1 (88899-55-2)

Guidance literature:

With tris(dimethylamino)sulfonium trimethylsilyldifluoride; water; In N,N-dimethyl-formamide; at 23 ℃;

DOI:10.1021/ja017885e

Reference yield: 93.0%

(3Z,5E,11E,13E)-(7R,8S,9S,15S,16R)-16-[(1R,2R,3S,6R,7S,8R)-2,8-Bis-(tert-butyl-dimethyl-silanyloxy)-6-hydroxy-1,3,7,9-tetramethyl-4-oxo-decyl]-3,15-dimethoxy-5,7,9,11-tetramethyl-8-triethylsilanyloxy-oxacyclohexadeca-3,5,11,13-tetraen-2-one (243468-81-7) → bafilomycin A1 (88899-55-2)

Guidance literature:

With tris(dimethylamino)sulfonium trimethylsilyldifluoride; water; In N,N-dimethyl-formamide; for 4h; Ambient temperature;

DOI:10.1002/(SICI)1521-3773(19990601)38:11<1652::AID-ANIE1652>3.0.CO;2-K

upstream raw materials:

C₅₀H₉₀O₉Si₂

(3Z,5E,11E,13E)-(7R,8S,9S,15S,16R)-16-[(1R,2R,3S,6R,7S,8R)-2,8-Bis-(tert-butyl-dimethyl-silanyloxy)-6-hydroxy-1,3,7,9-tetramethyl-4-oxo-decyl]-3,15-dimethoxy-5,7,9,11-tetramethyl-8-triethylsilanyloxy-oxacyclohexadeca-3,5,11,13-tetraen-2-one

(3Z,5E,11E,13E)-(7R,8S,9S,15S,16R)-16-{(1S,2R,3S)-3-[2-((2R,3S,4R)-2,4-Dihydroxy-3,5-dimethyl-hexyl)-[1,3]dithian-2-yl]-2-hydroxy-1-methyl-butyl}-8-hydroxy-3,15-dimethoxy-5,7,9,11-tetramethyl-oxacyclohexadeca-3,5,11,13-tetraen-2-one

(3S,4S)-4-[(benzyloxy)methoxy]-5-(tert-butyldiphenylsilanyloxy)-3-methylpentanoic acid methyl ester

Downstream raw materials:

bafilomycin A2

C₄₂H₆₂O₁₀

C₃₇H₆₀O₁₀

monoacetyl-bafilomycin-A₁

Refernces

• 1、 Kleinbeck, Florian,Carreira, Erick M.. "Total synthesis of bafilomycin A1". supporting information; experimental part. p. 578 - 581. Retrieved 2009/04/14.
• 2、 Hanessian,Ma,Wang. "Total synthesis of bafilomycin A1 relying on iterative 1,2-induction in acyclic precursors". . p. 10200 - 10206. Retrieved 2007/10/03.