1-Hydroxybenzotriazole → Boc-Glu(OtBu)-Ser(tBu)-Asn-Gly

HRID 2407054Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2407054
C1C=CC2N([OH:10])N=NC=2C=1.[NH:11]1CCC[CH2:13][CH2:12]1.C[N:18]([CH:20]=[O:21])[CH3:19].[NH:22]([C:31](OCC1C2C(=CC=CC=2)C2C1=CC=CC=2)=[O:32])[C@H:23]([C:28]([OH:30])=[O:29])CC(=O)N.[NH:48]([C:59]([O:61]CC1C2C(=CC=CC=2)C2C1=CC=CC=2)=O)[C@H:49](C(O)=O)[CH2:50][O:51][C:52]([CH3:55])([CH3:54])[CH3:53].[NH:76]([C:90]([O:92][C:93]([CH3:96])([CH3:95])[CH3:94])=[O:91])[C@H:77](C(O)=O)[CH2:78][CH2:79][C:80](=[O:86])[O:81][C:82]([CH3:85])([CH3:84])[CH3:83]>CN(C=O)C>[NH:76]([C:90]([O:92][C:93]([CH3:94])([CH3:95])[CH3:96])=[O:91])[C@H:77]([C:59]([NH:48][C@H:49]([C:20]([NH:18][C@H:19]([C:31]([NH:22][CH2:23][C:28]([OH:30])=[O:29])=[O:32])[CH2:13][C:12](=[O:10])[NH2:11])=[O:21])[CH2:50][O:51][C:52]([CH3:53])([CH3:54])[CH3:55])=[O:61])[CH2:78][CH2:79][C:80](=[O:86])[O:81][C:82]([CH3:83])([CH3:84])[CH3:85]

Komponenten

7

Edukt 5

HCID 757711-HydroxybenzotriazoleHCID 2724633N-(9-Fluorenylmethoxycarbonyl)-O-tert-butylserineHCID 2724774FMOC-L-asparagineHCID 6993432(2S)-5-(tert-butoxy)-2-{[(tert-butoxy)carbonyl]amino}-5-oxopentanoic acidHCID 23501187piperidine N,N-dimethylformamide

Produkt 1

HCID 131731781Boc-Glu(OtBu)-Ser(tBu)-Asn-Gly

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

An amino acid whose amino group had been protected, HOBt (67.6 mg, 0.50 mmol), and DIPCI (77.0 μL, 63.1 mg, 0.50 mmol) were dissolved in DMF (2 mL), and the obtained solution was then activated for 15 minutes. Thereafter, the solution was placed in the solid-phase synthesis column. After stirring at 25° C. for 1 hour, the Fmoc group was treated with a 20% piperidine/DMF solution (2 mL) for 20 minutes for deprotection. These operations were repeated, so that amino acids were successively condensed. As the protected amino acids, Fmoc-Asn (177.2 mg, 0.50 mmol), Fmoc-Ser(tBu) (191.6 mg, 0.50 mmol), and Boc-Glu(OtBu) (151.6 mg, 0.50 mmol) were used. On the solid-phase resin, a 4-residue peptide having a protecting group, Boc-Glu(OtBu)-Ser(tBu)-Asn-Gly (SEQ ID NO: 33), was obtained.

Aufarbeitung

  1. customThereafter, the solution was placed in the solid-phase synthesis column
  2. customcondensed

Quellen und Nachweise

ORD-Eintrag
ord-3d20b491acde4ba49a4f3deaecaa6d6b
Quelldatensatz
uspto-grants-2014_08
Patentnummer
US08809258B2

Notizen zur Reaktion

Wird geladen…