| Identification | Back Directory | [Name]
ASPERPHENAMATE | [CAS]
63631-36-7 | [Synonyms]
Auranamide
ASPERPHENAMATE
N-Benzoyl-L-phenylalanine (S)-2-benzoylamino-3-phenylpropyl ester
(2S)-2-(Benzoylamino)-3-phenylpropanoic acid (2S)-2-(benzoylamino)-3-phenylpropyl ester | [MDL Number]
MFCD30180097 | [MOL File]
63631-36-7.mol |
| Chemical Properties | Back Directory | [storage temp. ]
Store at -20°C | [solubility ]
DMF: soluble; DMSO: soluble; Ethanol: soluble; Methanol: soluble | [form ]
A solid | [color ]
White to off-white |
| Hazard Information | Back Directory | [Description]
Asperphenamate is a fungal secondary metabolite originally isolated from A. flavipes. It inhibits proliferation of T47D and MDA-MB-231 breast and HL-60 leukemia cancer cell lines (IC50s = 92.3, 96.5, and 97.9 μM, respectively) and inhibits yeast α-glucosidase activity (IC50 = 8.3 μM). | [Uses]
Asperphenamate is an α-glucosidase inhibitor isolated from Penicillium spathulatum. Asperphenamate exhibits anticancer properties and is used to synthesize N-Benzoyl-O-(N''-(1-benzyloxycarbonyl-4-piperidiylcarbonyl)-D-phenylalanyl)-D-phenylalaninol (BBP), an asperphenamate derivative that inhibits human breast carcinoma MCF-7 cell growth. | [Definition]
ChEBI: Asperphenamate is a carboxylic ester resulting from the formal condensation of the carboxy group of N-benzoyl-L-phenylalanine with the hydroxy group of N-benzoyl-L-phenylalaninol. A metabolite found in several Pencillium and Aspergillus species, as well as in plants as a product of endophytic fungi. It has a role as an antineoplastic agent. It is a L-phenylalanine derivative, a member of benzamides and a carboxylic ester. It is functionally related to a N-benzoyl-L-phenylalanine and a N-benzoyl-L-phenylalaninol. | [References]
[1] ALICE M. CLARK Charles D H. Synthesis of asperphenamate, a novel fungal metabolite[J]. Phytochemistry, 1978, 17 3: Pages 552-553. DOI: 10.1016/s0031-9422(00)89363-2
[2] LEI YUAN Tie M S Jin Hui Wang. Total synthesis and anticancer activity studies of the stereoisomers of asperphenamate and patriscabratine[J]. Chinese Chemical Letters, 2010, 21 2: Pages 155-158. DOI: 10.1016/j.cclet.2009.10.004
[3] PAULINA DEL VALLE. Alkaloids from the Fungus Penicillium spathulatum as α-Glucosidase Inhibitors.[J]. Planta medica, 2016, 82 14: 1286-1294. DOI: 10.1055/s-0042-111393 |
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