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MedKoo Cat#: 463386 | Name: Aculeacin A

Description:

WARNING: This product is for research use only, not for human or veterinary use.

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. 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.

Chemical Structure

Aculeacin A
Aculeacin A
CAS#58814-86-1

Theoretical Analysis

MedKoo Cat#: 463386

Name: Aculeacin A

CAS#: 58814-86-1

Chemical Formula: C51H82N8O17

Exact Mass: 1078.5798

Molecular Weight: 1079.26

Elemental Analysis: C, 56.76; H, 7.66; N, 10.38; O, 25.20

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
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Synonym
Aculeacin A; Aculeacin-A;
IUPAC/Chemical Name
N-((2R,6S,9S,11R,12R,14aS,15S,16S,20S,23S,25aS)-20-((R)-3-amino-1-hydroxy-3-oxopropyl)-23-((1S,2S)-1,2-dihydroxy-2-(4-hydroxyphenyl)ethyl)-2,11,12,15-tetrahydroxy-6-((R)-1-hydroxyethyl)-16-methyl-5,8,14,19,22,25-hexaoxotetracosahydro-1H-dipyrrolo[2,1-c:2',1'-l][1,4,7,10,13,16]hexaazacyclohenicosin-9-yl)palmitamide
InChi Key
FBCLKBXYZRAXNA-PDIPHZEPSA-N
InChi Code
InChI=1S/C51H82N8O17/c1-4-5-6-7-8-9-10-11-12-13-14-15-16-17-37(66)53-32-23-35(64)47(72)57-49(74)41-42(67)27(2)25-59(41)51(76)39(34(63)24-36(52)65)55-48(73)40(44(69)43(68)29-18-20-30(61)21-19-29)56-46(71)33-22-31(62)26-58(33)50(75)38(28(3)60)54-45(32)70/h18-21,27-28,31-35,38-44,47,60-64,67-69,72H,4-17,22-26H2,1-3H3,(H2,52,65)(H,53,66)(H,54,70)(H,55,73)(H,56,71)(H,57,74)/t27-,28+,31+,32-,33-,34+,35+,38-,39-,40-,41-,42-,43-,44-,47+/m0/s1
SMILES Code
CCCCCCCCCCCCCCCC(N[C@H]1C[C@H]([C@H](NC([C@@H]2[C@H]([C@H](CN2C([C@H]([C@@H](CC(N)=O)O)NC([C@H]([C@@H]([C@H](c3ccc(O)cc3)O)O)NC([C@@H]4C[C@H](CN4C([C@H]([C@H](O)C)NC1=O)=O)O)=O)=O)=O)C)O)=O)O)O)=O
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 1,079.26 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Zhang F, Liu H, Zhang T, Pijning T, Yu L, Zhang W, Liu W, Meng X. Biochemical and genetic characterization of fungal proline hydroxylase in echinocandin biosynthesis. Appl Microbiol Biotechnol. 2018 Sep;102(18):7877-7890. doi: 10.1007/s00253-018-9179-y. Epub 2018 Jul 9. PMID: 29987385. 2: Isogai Y, Nakayama K. Alteration of substrate selection of antibiotic acylase from β-lactam to echinocandin. Protein Eng Des Sel. 2016 Feb;29(2):49-56. doi: 10.1093/protein/gzv059. Epub 2015 Nov 19. PMID: 26590167. 3: Velasco-Bucheli R, Del Cerro C, Hormigo D, Acebal C, Arroyo M, García JL, de la Mata I. Draft Genome Sequence of Actinoplanes utahensis NRRL 12052, a Microorganism Involved in Industrial Production of Pharmaceutical Intermediates. Genome Announc. 2015 Jan 8;3(1):e01411-14. doi: 10.1128/genomeA.01411-14. PMID: 25573944; PMCID: PMC4290995. 4: van Wanrooy MJ, Santoe RN, van der Elst KC, Wilmer CM, van Hateren K, Wessels AM, Greijdanus B, Alffenaar JW, Uges DR. Simultaneous quantification of anidulafungin and caspofungin in plasma by an accurate and simple liquid chromatography tandem mass-spectrometric method. Ther Drug Monit. 2013 Dec;35(6):778-84. doi: 10.1097/FTD.0b013e31829591a7. PMID: 24081203. 5: Ueda S, Shibata T, Ito K, Oohata N, Yamashita M, Hino M, Yamada M, Isogai Y, Hashimoto S. Cloning and expression of the FR901379 acylase gene from Streptomyces sp. no. 6907. J Antibiot (Tokyo). 2011 Feb;64(2):169-75. doi: 10.1038/ja.2010.151. Epub 2010 Dec 1. PMID: 21119679. 6: Ma CM, Abe T, Komiyama T, Wang W, Hattori M, Daneshtalab M. Synthesis, anti- fungal and 1,3-β-D-glucan synthase inhibitory activities of caffeic and quinic acid derivatives. Bioorg Med Chem. 2010 Oct 1;18(19):7009-14. doi: 10.1016/j.bmc.2010.08.022. Epub 2010 Aug 13. PMID: 20813534. 7: Hormigo D, de la Mata I, Acebal C, Arroyo M. Immobilized aculeacin A acylase from Actinoplanes utahensis: characterization of a novel biocatalyst. Bioresour Technol. 2010 Jun;101(12):4261-8. doi: 10.1016/j.biortech.2010.01.117. Epub 2010 Feb 25. PMID: 20188542. 8: Chen CN, Chen CJ, Liao CT, Lee CY. A probable aculeacin A acylase from the Ralstonia solanacearum GMI1000 is N-acyl-homoserine lactone acylase with quorum- quenching activity. BMC Microbiol. 2009 May 9;9:89. doi: 10.1186/1471-2180-9-89. PMID: 19426552; PMCID: PMC2686713. 9: Torres-Bacete J, Hormigo D, Stuart M, Arroyo M, Torres P, Castillón MP, Acebal C, García JL, de la Mata I. Newly discovered penicillin acylase activity of aculeacin A acylase from Actinoplanes utahensis. Appl Environ Microbiol. 2007 Aug;73(16):5378-81. doi: 10.1128/AEM.00452-07. Epub 2007 Jun 22. PMID: 17586674; PMCID: PMC1950969. 10: Zhang D, Koreishi M, Imanaka H, Imamura K, Nakanishi K. Cloning and characterization of penicillin V acylase from Streptomyces mobaraensis. J Biotechnol. 2007 Mar 10;128(4):788-800. doi: 10.1016/j.jbiotec.2006.12.017. Epub 2007 Jan 10. PMID: 17289203. 11: Selvakumar D, Karim N, Miyamoto M, Furuichi Y, Komiyama T. Recombinant single-chain anti-idiotypic antibody: an effective fungal beta-1,3-glucan synthase inhibitor. Biol Pharm Bull. 2006 Sep;29(9):1848-53. doi: 10.1248/bpb.29.1848. PMID: 16946497. 12: Romero M, Cantón E, Pemán J, Gobernado M. Antifúngicos inhibidores de la síntesis del glucano [Antifungal inhibitors of glucan synthesis]. Rev Esp Quimioter. 2005 Dec;18(4):281-99. Spanish. PMID: 16446788. 13: Tanaka H, Kamogawa T, Aoyagi H, Kato I, Nakajima R. Invertase production by Saccharomyces cerevisiae protoplasts immobilized in strontium alginate gel beads. J Biosci Bioeng. 2000;89(5):498-500. doi: 10.1016/s1389-1723(00)89105-7. PMID: 16232786. 14: Lin YH, Xu JL, Hu J, Wang LH, Ong SL, Leadbetter JR, Zhang LH. Acyl- homoserine lactone acylase from Ralstonia strain XJ12B represents a novel and potent class of quorum-quenching enzymes. Mol Microbiol. 2003 Feb;47(3):849-60. doi: 10.1046/j.1365-2958.2003.03351.x. PMID: 12535081. 15: Komiyama T, Kimura T, Furuichi Y. Round shape enlargement of the yeast spheroplast of Saccharomyces cerevisiae by HM-1 toxin. Biol Pharm Bull. 2002 Aug;25(8):959-65. doi: 10.1248/bpb.25.959. PMID: 12186426. 16: Fujie A, Iwamoto T, Muramatsu H, Okudaira T, Nitta K, Nakanishi T, Sakamoto K, Hori Y, Hino M, Hashimoto S, Okuhara M. FR901469, a novel antifungal antibiotic from an unidentified fungus No.11243. I. Taxonomy, fermentation, isolation, physico-chemical properties and biological properties. J Antibiot (Tokyo). 2000 Sep;53(9):912-9. doi: 10.7164/antibiotics.53.912. PMID: 11099224. 17: Komiyama T, Shirai T, Ohta T, Urakami H, Furuichi Y, Ohta Y, Tsukada Y. Action properties of HYI killer toxin from Williopsis saturnus var. saturnus, and antibiotics, aculeacin A and papulacandin B. Biol Pharm Bull. 1998 Oct;21(10):1013-9. doi: 10.1248/bpb.21.1013. PMID: 9821802. 18: Wood RL, Miller TK, Wright A, McCarthy P, Taft CS, Pomponi S, Selitrennikoff CP. Characterization and optimization of in vitro assay conditions for (1,3)beta-glucan synthase activity from Aspergillus fumigatus and Candida albicans for enzyme inhibition screening. J Antibiot (Tokyo). 1998 Jul;51(7):665-75. doi: 10.7164/antibiotics.51.665. PMID: 9727393. 19: Osumi M. The ultrastructure of yeast: cell wall structure and formation. Micron. 1998 Apr-Jun;29(2-3):207-33. doi: 10.1016/s0968-4328(97)00072-3. PMID: 9684351. 20: Castro C, Ribas JC, Valdivieso MH, Varona R, del Rey F, Duran A. Papulacandin B resistance in budding and fission yeasts: isolation and characterization of a gene involved in (1,3)beta-D-glucan synthesis in Saccharomyces cerevisiae. J Bacteriol. 1995 Oct;177(20):5732-9. doi: 10.1128/jb.177.20.5732-5739.1995. PMID: 7592316; PMCID: PMC177391.

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