Ethanaminide → N-Ac-Lys(Ac)-Cit-NHCH2CH3

HRID 891474Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 891474
N1(C(OCC2C3C(=CC=CC=3)C3C2=CC=CC=3)=O)CCC[C@H:2]1[C:3](O)=[O:4].[CH2:26]([NH-:28])[CH3:27].N(C(OCC1C2C(=CC=CC=2)C2C1=CC=CC=2)=O)[C@H](C(O)=O)C[CH2:32][CH2:33][CH2:34][NH:35][C:36]([CH3:38])=[O:37].[NH:59](C(OCC1C2C(=CC=CC=2)C2C1=CC=CC=2)=O)[C@H:60](C(O)=O)[C@H:61](CC)C.[NH:85]([C:115]([O:117]CC1C2C(=CC=CC=2)C2C1=CC=CC=2)=O)[C@H:86]([C:112]([OH:114])=O)[CH2:87][CH2:88][CH2:89][NH:90][C:91](=[NH:111])NS(C1C(C)=C(C)C2OC(C)(C)CCC=2C=1C)(=O)=O.C(O)(C(F)(F)F)=[O:133].C1(OC)C=CC=CC=1.O>>[NH:28]([C:3]([CH3:2])=[O:4])[C@H:26]([C:115]([NH:85][C@H:86]([C:112]([NH:59][CH2:60][CH3:61])=[O:114])[CH2:87][CH2:88][CH2:89][NH:90][C:91]([NH2:111])=[O:133])=[O:117])[CH2:27][CH2:32][CH2:33][CH2:34][NH:35][C:36]([CH3:38])=[O:37]

Komponenten

7

Edukt 6

HCID 187872EthanaminideHCID 688135Fmoc-Pro-OHHCID 2724629N-Fmoc-L-isoleucineHCID 7018846Fmoc-Lys(Ac)-OHHCID 131725292TFA anisole waterHCID 178427573HCID 178427573, Verbindung

Produkt 1

HCID 10201877N-Ac-Lys(Ac)-Cit-NHCH2CH3

Versuchsvorschrift

The procedure described in Example 1 can used but substituting Fmoc-Cit-[4-(4-N-ethyl)methyl-3-methoxyphenoxy]butyryl AM resin for Fmoc-Pro Sieber ethylamide resin, Fmoc-Lys(Ac) for Fmoc-Ile and omitting the coupling with Fmoc-Arg(Pmc). Upon completion of the synthesis the peptide can be cleaved from the resin using a mixture of (95:2.5:2.5) TFA/anisole/water for 3 hr. The peptide solution can be concentrated in vacuo and then precipitated with diethyl ether. The crude peptide can be purified by HPLC using C-18 column and with a solvent mixture varying over 50 minutes in a gradient from 5% to 100% acetonitrile-water containing 0.01% TFA. The pure fractions can be lyophilized to give N-Ac-Lys(Ac)-Cit-NHCH2CH3.

Aufarbeitung

  1. concentrationThe peptide solution can be concentrated in vacuo
  2. customprecipitated with diethyl ether
  3. customThe crude peptide can be purified by HPLC

Quellen und Nachweise

ORD-Eintrag
ord-791e5c91c9424a98af38b64ee9456ff8
Quelldatensatz
uspto-grants-2006_02
Patentnummer
US07001984B2

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