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A7603

Sigma-Aldrich

Aculeacin A

from Aspergillus aculeatus, ≥95% (HPLC)

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About This Item

Empirical Formula (Hill Notation):
C50H81N7O16
CAS Number:
58814-86-1
Molecular Weight:
1036.22
MDL number:
MFCD01674009
UNSPSC Code:
41116107
PubChem Substance ID:
329770935
NACRES:
NA.85

biological source

Aspergillus aculeatus

Quality Level

200

assay

≥95% (HPLC)

form

powder

solubility

DMSO: 10 mg/mL
DMF: soluble
ethanol: soluble
methanol: soluble

antibiotic activity spectrum

yeast

mode of action

cell wall synthesis | interferes

shipped in

wet ice

storage temp.

−20°C

SMILES string

CCCCCCCCCCCCCCCC(=O)N[C@H]1C[C@@H](O)[C@@H](O)NC(=O)[C@@H]2[C@@H](O)[C@@H](C)CN2C(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H]3C[C@@H](O)C[N@H]3C(=O)[C@@H](NC1=O)[C@@H](C)O)[C@H](O)[C@@H](O)c4ccc(O)cc4)[C@@H](C)O

InChI

1S/C50H81N7O16/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-36(63)51-33-24-35(62)46(69)55-48(71)40-41(64)27(2)25-57(40)50(73)38(29(4)59)53-47(70)39(43(66)42(65)30-19-21-31(60)22-20-30)54-45(68)34-23-32(61)26-56(34)49(72)37(28(3)58)52-44(33)67/h19-22,27-29,32-35,37-43,46,58-62,64-66,69H,5-18,23-26H2,1-4H3,(H,51,63)(H,52,67)(H,53,70)(H,54,68)(H,55,71)/t27-,28+,29+,32+,33-,34-,35+,37-,38-,39-,40-,41-,42-,43-,46+/m0/s1

InChI key

YKPHLXGEPNYRPY-ZIUFDZNVSA-N

Application

Aculeacin A is used to study mutations that lead to antibiotic resistance in Saccharomyces cerevisiae , the inhibition of Candida albicans, and the morphogenetic transformation of Candida albicans when treated .

Biochem/physiol Actions

Aculeacin A is a lipopeptide that inhibits β-glucan synthesis in yeasts. The inhibition is due to the selective blockage of glucan synthase.
Aculeacin A, an amphophilic antibiotic, inhibits the biosynthesis of β−glucan by selective blockage of β(1→3) glucan synthase.

Other Notes

Keep container tightly closed in a dry and well-ventilated place.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 2

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Y Matsumoto et al.
The Journal of protozoology, 38(6), 6S-7S (1991-11-01)
Pneumocystis pneumonia is the most serious opportunistic infection in immunocompromised patients, particularly those with AIDS. Approved therapy is limited to pentamidine and inhibitors of folic acid synthesis, but these drugs show a high rate of adverse reactions in AIDS patients
[Antifungal inhibitors of glucan synthesis].
M Romero et al.
Revista espanola de quimioterapia : publicacion oficial de la Sociedad Espanola de Quimioterapia, 18(4), 281-299 (2006-02-01)
Susceptibility of Candida species isolated from the oral region to aculeacin A.
K Mitsui et al.
Hiroshima Daigaku shigaku zasshi. The Journal of Hiroshima University Dental Society, 17(2), 315-317 (1985-12-01)
Jesús Torres-Bacete et al.
Applied and environmental microbiology, 73(16), 5378-5381 (2007-06-26)
Aculeacin A acylase from Actinoplanes utahensis produced by Streptomyces lividans revealed acylase activities that are able to hydrolyze penicillin V and several natural aliphatic penicillins. Penicillin K was the best substrate, showing a catalytic efficiency of 34.79 mM(-1) s(-1). Furthermore
Cilofungin inhibition of (1-3)-beta-glucan synthase: the lipophilic side chain is essential for inhibition of enzyme activity.
C S Taft et al.
The Journal of antibiotics, 43(4), 433-437 (1990-04-01)
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