Aureobasidin A | CAS No. 127785-64-2

Aureobasidin A

Basic Information

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CAS Number

127785-64-2

Molecular Formula

C60H92N8O11

Molecular Weight

1101.44 g/mol

Chemical Classification

Basic Chemical Raw Materials Organic Chemicals Carboxylic Acids

Basic Chemical Raw Materials Organic Chemicals Esters

Basic Chemical Raw Materials Organic Chemicals Ethers

Basic Chemical Raw Materials Organic Chemicals Heterocyclic Compounds

Pharmaceutical Chemicals Pharmaceutical Intermediates Heterocyclic Intermediates

Fine Chemicals Dyes and Pigments Organic Dyes

Fine Chemicals Surfactants Anionic Surfactants

Laboratory Chemicals Research Chemicals Biochemical Reagents

Basic Physical Properties

SMILES

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CCC(C)C1C(=O)N(C(C(=O)NC(C(=O)N(C(C(=O)OC(C(=O)N(C(C(=O)NC(C(=O)N(C(C(=O)N2CCCC2C(=O)N1)CC3=CC=CC=C3)C)CC4=CC=CC=C4)C(C)C)C)C(C)CC)C(C)(C)O)C)CC(C)C)C(C)C)C

InChI

InChI=1S/C60H92N8O11/c1-17-38(9)46-57(75)65(14)47(36(5)6)52(70)61-42(32-35(3)4)55(73)67(16)50(60(11,12)78)59(77)79-49(39(10)18-2)58(76)66(15)48(37(7)8)53(71)62-43(33-40-26-21-19-22-27-40)54(72)64(13)45(34-41-28-23-20-24-29-41)56(74)68-31-25-30-44(68)51(69)63-46/h19-24,26-29,35-39,42-50,78H,17-18,25,30-34H2,1-16H3,(H,61,70)(H,62,71)(H,63,69)/t38-,39-,42+,43+,44+,45+,46+,47+,48+,49-,50-/m1/s1

InChIKey

RLMLFADXHJLPSQ-QKCBWMAHSA-N

LogP

4.3718000000000075

Topological Polar Surface Area

235.38 Å²

Hydrogen Bond Donor/Acceptor

4 / 19

Complexity

2110

Synonyms & References

English

NS00011675
R106-1
N-((2R,3R)-2-HYDROXY-3-METHYLVALERYL)-N-METHYL-L-VALYL-L-PHENYLALANYL-N-METHYL-L-PHENYLALANYL-L-PROLYL-L-ALLOISOLEUCYL-N-METHYL-L-VALYL-L-LEUCYL-3-HYDROXY-N-METHYL-L-VALINE .ALPHA.(SUB 1)-LACTONE
Basifungin [USAN:INN]
R106 1
VV0USO6I6U
(3S,6S,9S,12R,15S,18S,21S,24S,27S)-3,6-dibenzyl-12,24-bis[(2R)-butan-2-yl]-15-(2-hydroxypropan-2-yl)-4,10,16,22-tetramethyl-18-(2-methylpropyl)-9,21-di(propan-2-yl)-13-oxa-1,4,7,10,16,19,22,25-octazabicyclo[25.3.0]triacontane-2,5,8,11,14,17,20,23,26-nonone
Basifungin; AbA
MS-31962
NK 204
DTXSID201017531
Valine, 3-hydroxy-N-(N-(N-(N-(1-(N-(N-(N-(2-hydroxy-3-methyl-1-oxopentyl)-N-methylvalyl)phenylalanyl)-N-methylphenylalanyl)prolyl)alloisoleucyl)-N-methylvalyl)leucyl)-N-methyl-, alpha-1-lactone
BASIFUNGIN [USAN]
Basifungin
SCHEMBL301215
LY-295337
N-((2R,3R)-2-Hydroxy-3-methylvaleryl)-N-methyl-L-valyl-L-phenylalanyl-N-methyl-L-phenylalanyl-L-prolyl-L-alloisoleucyl-N-methyl-L-valyl-L-leucyl-3-hydroxy-N-methyl-L-valine alpha1-lactone
Q27292033
Ly 295337
Aureobasidin A
BDBM50408926
CS-0104069
UNII-VV0USO6I6U
NK-204
D03057
HY-P1975
CHEMBL1793802
BASIFUNGIN [INN]
Aureobasidin A pound notAbA
Basifungin (USAN/INN)
R-106-1

MDL Number

MFCD00865571

FAQ

What are the physical and chemical properties of Aureobasidin A (CAS: 127785-64-2)?

Aureobasidin A (CAS: 127785-64-2) is a cyclic depsipeptide with a molecular weight of approximately 506.4 g/mol. It is sparingly soluble in water but highly soluble in organic solvents like methanol and acetonitrile. Chemically, it exhibits moderate reactivity towards nucleophiles and is stable under acidic and neutral conditions but can be degraded under basic conditions. Its crystalline form has been characterized by X-ray crystallography, revealing a unique cyclic structure with specific hydrogen bonding patterns.

How is Aureobasidin A (CAS: 127785-64-2) typically synthesized?

Aureobasidin A (CAS: 127785-64-2) is typically synthesized through a multi-step chemical process involving peptide coupling, amidation, and cyclization reactions. The key synthetic route involves the condensation of suitable amino acids, followed by peptide bond formation and cyclization. The use of catalysts such as HOBt and DCC is common to enhance reactivity and selectivity. The overall yield is around 40-50%, and the method is known for its high chemical and enantioselectivity.

What industries use Aureobasidin A (CAS: 127785-64-2)?

Aureobasidin A (CAS: 127785-64-2) finds applications in various industries. In pharmaceuticals, it has potential as an antifungal agent. It is also used in polymer synthesis as a molecular weight regulator, in sensor technology for detection of specific biomarkers, and in semiconductor manufacturing for quality control. Its bioactive properties make it valuable in both research and commercial applications.

What precautions should be taken when handling Aureobasidin A (CAS: 127785-64-2)?

When handling Aureobasidin A (CAS: 127785-64-2), it is essential to wear appropriate personal protective equipment (PPE), including gloves, goggles, and a lab coat. Work should be conducted in a well-ventilated area or a fume hood to minimize inhalation risks. In case of skin contact, immediately wash the affected area with soap and water. If swallowed, do not induce vomiting and seek medical attention. Keep the compound away from sources of heat and ensure proper storage in a cool, dry place. Always consult the Material Safety Data Sheet (MSDS) for detailed safety information and emergency procedures.