Phenylacetyl-L-Glutamine (PAGLN)

Basic information

  • Product Name:Phenylacetyl-L-Glutamine (PAGLN)
  • CasNo.:28097-03-2
  • MF:C30H28 N6 O6 S4
  • MW:696.853

Physical and Chemical Properties

  • Purity:99%
  • Boiling Point:
  • Packing:
  • Throughput:
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Product Details

CasNo: 28097-03-2

MF: C30H28 N6 O6 S4

Buy Quality Phenylacetyl-L-Glutamine (PAGLN) 28097-03-2 In Stock with Immediately Delivery

  • Molecular Formula:C30H28N6O6S4
  • Molecular Weight:696.853
  • Boiling Point:°Cat760mmHg 
  • PKA:12.39±0.10(Predicted) 
  • Flash Point:°C 
  • PSA:246.96000 
  • Density:1.87g/cm3 
  • LogP:1.36160 

CHAETOCIN FROM CHAETOMIUM MINUTUM(Cas 28097-03-2) Usage

Biochem/physiol Actions

Chaetocin is a competitive inhibitor for S-adenosylmethionine. The specificity of chaetocin for SU(VAR)3-9 makes CHAETOCIN FROM CHAETOMIUM MINUTUM an excellent tool for the study of heterochromatin-mediated gene repression.

Application

Chaetocin is a natural metabolite isolated from Chaetomium minutum. It is a nonspecific inhbitor of histone lysine methyltransferases which are important epigenetic enzymes . Induces apoptosis in myeloma cell lines and exhibits antiproliferative activity in mammals. Chaetocin from Chaetomium minutum has been used to determine its effects on sensitization of various cells. It has also been used to determine the biological functions of OS-induced heterochromatin formation.

General Description

Chaetocin is a fungal metabolite with antimicrobial and cytostatic activity. It belongs to the 3,6-epidithio-diketopiperazines class of which gliotoxin, sporidesmin, aranotin, oryzachloride, verticillin A and the melinacidins are members. Chaetocin is a molecular dimer of two five-membered rings cis fused. Interestingly, the chirality of the 3,6-epidithiodioxopiperazine moiety in chaetocin is opposite to the chirality of gliotoxin, sporidesmin, aranotin, and oryzachloride. Unlike these compounds, chaetocin does not have an antiviral activity. This fungal toxin showed strong cytotoxicity against HeLa cells (IC50 = 0.05 mg/ml).

InChI:InChI=1/C30H28N6O6S4/c1-33-21(39)27-11-25(15-7-3-5-9-17(15)31-19(25)35(27)23(41)29(33,13-37)45-43-27)26-12-28-22(40)34(2)30(14-38,46-44-28)24(42)36(28)20(26)32-18-10-6-4-8-16(18)26/h3-10,19-20,31-32,37-38H,11-14H2,1-2H3

28097-03-2 Relevant articles

Epidithiodiketopiperazine as a pharmacophore for protein lysine methyltransferase G9a inhibitors: Reducing cytotoxicity by structural simplification

Fujishiro, Shinya,Dodo, Kosuke,Iwasa, Eriko,Teng, Yuou,Sohtome, Yoshihiro,Hamashima, Yoshitaka,Ito, Akihiro,Yoshida, Minoru,Sodeoka, Mikiko

, p. 733 - 736 (2013/03/13)

Chaetocin (1), a structurally complex ep...

Total synthesis of (+)-chaetocin and its analogues: Their histone methyltransferase g9a inhibitory activity

Iwasa, Eriko,Hamashima, Yoshitaka,Fujishiro, Shinya,Eisuke, Higuchi,Ito, Akihiro,Yoshida, Minoru,Sodeoka, Mikiko

supporting information; experimental part, p. 4078 - 4079 (2010/05/15)

Chemical Equation Presentation The first...

General approach to epipolythiodiketopiperazine alkaloids: Total synthesis of (+)-chaetocins A and C and (+)-12,12′-dideoxychetracin A

Kim, Justin,Movassaghi, Mohammad

supporting information; experimental part, p. 14376 - 14378 (2010/12/24)

A highly stereoselective and systematic ...

Chetracin A and chaetocins B and C, three new epipolythiodioxopiperazines from Chaetomium spp.

Saito,Suzuki,Koyama,Natori,Iitaka,Kinoshita

, p. 1942 - 1956 (2007/10/02)

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28097-03-2 Process route

(+)-chaetocin A diacetate
28097-04-3

(+)-chaetocin A diacetate

chaetocin
28097-03-2

chaetocin

Conditions
Conditions Yield
With methanol; Otera's catalyst; In toluene; at 85 ℃; for 7.33333h; Inert atmosphere;
92%
C<sub>52</sub>H<sub>76</sub>N<sub>6</sub>O<sub>14</sub>Si<sub>2</sub>
1219135-51-9

C52H76N6O14Si2

chaetocin
28097-03-2

chaetocin

Conditions
Conditions Yield
C52H76N6O14Si2; With boron trifluoride diethyl etherate; hydrogen sulfide; In dichloromethane; at -78 - 20 ℃; Sealed tube;
With iodine; In ethyl acetate; at 20 ℃; for 0.0166667h;
44%
Multi-step reaction with 2 steps
1: hydrogen sulfide; boron trifluoride diethyl etherate / dichloromethane / -78 - -20 °C
2: iodine / ethyl acetate
With boron trifluoride diethyl etherate; hydrogen sulfide; iodine; In dichloromethane; ethyl acetate;

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    C52H76N6O14Si2

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    1219135-73-5

    C52H76N6O14Si2