2-(6-Hydroxy-3-oxo-3H-xanthen-9-yl)benzoic acid → HCID 178512911, Verbindung

HRID 1766107Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1766107
CC[C@@H]([C@H](NC([C@@H](N[C:149]([C@@H:151]([NH2:159])[CH2:152][CH2:153][CH2:154][NH:155][C:156]([NH2:158])=[NH:157])=[O:150])CCC(N)=O)=O)C(N[C@H](C(N[C@H](C(N[C@H](C(N[C@H](C(N[C@H](C(N[C@H](C(N[C@H](C(N[C@H](C(N[C@H](C(N[C@H](C(N[C@H](C(N[C@H](C(N[C@H](C(O)=O)CCCCN)=O)CCCCN)=O)CC1C2C(=CC=CC=2)NC=1)=O)CCCCN)=O)CCSC)=O)CCCNC(N)=N)=O)CCCNC(N)=N)=O)CC(N)=O)=O)CCC(N)=O)=O)CC1C=CC=CC=1)=O)CC1C2C(=CC=CC=2)NC=1)=O)[C@H](CC)C)=O)CCCCN)=O)C.N[C@H](C(O)=[O:170])CCCNC(=N)N.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C1C=CC(C(O)=O)=C(C2C3C=CC(O)=CC=3OC3C=2C=CC(C=3)=O)C=1.NC(CCCC)C(O)=O.C1C(N=C=S)=CC2C(OC3(C4C=CC(O)=CC=4OC4C=C(O)C=CC3=4)C=2C=1)=O.CCN(C(C)C)C(C)C.C(O)(C(F)(F)F)=O.C([SiH](C(C)C)C(C)C)(C)C>CN(C=O)C>[NH2:159][C@@H:151]([C:149]([OH:170])=[O:150])[CH2:152][CH2:153][CH2:154][NH:155][C:156](=[NH:157])[NH2:158]

Komponenten

10

Edukt 8

HCID 33832-(6-Hydroxy-3-oxo-3H-xanthen-9-yl)benzoic acidHCID 9475Norleucine, (+-)-HCID 18730Fluorescein 5-isothiocyanateHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 16135911RqikiwfqnrrmkwkkHCID 131724268TFA triisopropylsilaneHCID 178418600HCID 178418600, Verbindung

Produkt 1

HCID 178512911HCID 178512911, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

General Procedure for Peptide Synthesis. Tat49-57 (RKKRRQRRR; SEQ ID NO:28), truncated and alanine-substituted peptides derived from Tat49-57, Antennapedia43-58 (RQIKIWFQNRRMKWKK; SEQ ID NO:29), and homopolymers of arginine (R5–R9; SEQ ID NO:1–5) and d-arginine (r5-r9) were prepared with an automated peptide synthesizer (ABI433) using standard solid-phase Fmoc chemistry (35) with HATU as the peptide coupling reagent. The fluorescein moiety was attached via a aminohexanoic acid spacer by treating a resin-bound peptide (1.0 mmol) with fluorescein isothiocyanate (1.0 mmol) and DIEA (5 mmol) in DMF (10 mL) for 12 h. Cleavage from the resin was achieved using 95:5 TFA/triisopropylsilane. Removal of the solvent in vacuo gave a crude oil which was triturated with cold ether. The crude mixture thus obtained was centrifuged, the ether was removed by decantation, and the resulting orange solid was purified by reverse-phase HPLC (H2O/CH3CN in 0.1% TFA). The products were isolated by lyophilization and characterized by electrospray mass spectrometry. Purity of the peptides was >95% as determined by analytical reverse-phase HPLC (H2O/CH3CN in 0.1% TFA).

Aufarbeitung

  1. customRemoval of the solvent in vacuo
  2. customgave a crude oil which
  3. customwas triturated with cold ether

Quellen und Nachweise

ORD-Eintrag
ord-cdb09df517b6459b87b01e0005bfd423
Quelldatensatz
uspto-grants-2007_06
Patentnummer
US07229961B2

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