Asperlicin
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| Category | Mycotoxins |
| Catalog number | BBF-00112 |
| CAS | 93413-04-8 |
| Molecular Weight | 535.59 |
| Molecular Formula | C31H29N5O4 |
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Description
Asperlicin is a non-peptide cholecystokinin (Cholecystokinin, CCK) produced by Aspergillus alliaceus. It has the effect of antagonizing CCK. A and its derivatives are promising for the treatment of ulcers and pancreatic tumors.
Specification
| Synonyms | Asperlicin A |
| IUPAC Name | (7S)-7-[[(2S,3aS,4S)-4-hydroxy-2-(2-methylpropyl)-1-oxo-3,3a-dihydro-2H-imidazo[1,2-a]indol-4-yl]methyl]-6,7-dihydroquinazolino[3,2-a][1,4]benzodiazepine-5,13-dione |
| Canonical SMILES | CC(C)CC1C(=O)N2C(N1)C(C3=CC=CC=C32)(CC4C5=NC6=CC=CC=C6C(=O)N5C7=CC=CC=C7C(=O)N4)O |
| InChI | InChI=1S/C31H29N5O4/c1-17(2)15-22-29(39)36-25-14-8-5-11-20(25)31(40,30(36)34-22)16-23-26-32-21-12-6-3-9-18(21)28(38)35(26)24-13-7-4-10-19(24)27(37)33-23/h3-14,17,22-23,30,34,40H,15-16H2,1-2H3,(H,33,37)/t22-,23-,30-,31-/m0/s1 |
| InChI Key | MGMRIOLWEROPJY-FPACPZPDSA-N |
Properties
| Appearance | White Crystals |
| Melting Point | 211-213°C |
| Density | 1.48 g/cm3 |
| Solubility | Soluble in Dichloromethane, Acetone |
Reference Reading
1. Tin triflate-mediated total synthesis of circumdatin F, sclerotigenin, asperlicin C, and other quinazolino[3,2-a][1,4]benzodiazepines
Ming-Chung Tseng, Chi-Yu Lai, Yu-Wan Chu, Yen-Ho Chu Chem Commun (Camb). 2009 Jan 28;(4):445-7. doi: 10.1039/b813880j. Epub 2008 Nov 19.
Using tin triflate, as an effective Lewis acid, and microwaves, direct double cyclizations of bis(anthranilate)-containing tripeptide precursors to afford the total syntheses of 7-substituted quinazolino[3,2-a][1,4]benzodiazepinediones (1a-f), including natural products circumdatin F (1a), sclerotigenin (1b), and asperlicin C (1c), were achieved with good overall isolated yields (23-62%).
2. Total synthesis of asperlicin C, circumdatin F, demethylbenzomalvin A, demethoxycircumdatin H, sclerotigenin, and other fused quinazolinones
Ming-Chung Tseng, Huei-Yun Yang, Yen-Ho Chu Org Biomol Chem. 2010 Jan 21;8(2):419-27. doi: 10.1039/b910545j. Epub 2009 Nov 5.
Using scandium triflate and microwaves, the direct double dehydrocyclization of anthranilate-containing tripeptides was achieved, affording the total syntheses of (i) quinazolino[3,2-a]benzodiazepinediones (), (ii) diazepino[2,1-b]quinazolinediones (), and (iii) pyrazino[2,1-b]quinazolinediones () with good overall isolated yields (23-43%, 37-47% and 31-56%, respectively). Among the quinazolino[3,2-a]benzodiazepinediones synthesized, (sclerotigenin), (circumdatin F), and (asperlicin C) are natural products.
3. Assembly of asperlicin peptidyl alkaloids from anthranilate and tryptophan: a two-enzyme pathway generates heptacyclic scaffold complexity in asperlicin E
Stuart W Haynes, Xue Gao, Yi Tang, Christopher T Walsh J Am Chem Soc. 2012 Oct 24;134(42):17444-7. doi: 10.1021/ja308371z. Epub 2012 Oct 9.
Members of the asperlicin family of fungal metabolites produced by Aspergillus alliaceus are known potent CCK(A) antagonists. Herein, we report the identification of the gene cluster responsible for directing their biosynthesis. We validate and probe the pathway by genetic manipulation, and provide the first biochemical characterization of the oxidative cyclization en route to the heptacyclic asperlicin E by reconstituting the activity of the FAD depend monooxygenase AspB. This report provides the first genetic characterization of a NRPS assembly line that efficiently activates two anthranilate building blocks and illustrates the remarkably efficient biosynthesis of the complex heptacyclic asperlicin E.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
