Trifluoroacetic acid → Lys-Val-Lys

HRID 251316

Reaction equation

HRID 251316 reaction equation
CC(OC([NH:8][CH2:9][CH2:10][CH2:11][CH2:12][C@H:13]([NH2:17])[C:14]([OH:16])=[O:15])=O)(C)C.[NH:18]([C:26]([O:28]CC1C2C(=CC=CC=2)C2C1=CC=CC=2)=O)[C@H:19]([C:23]([OH:25])=O)[CH:20]([CH3:22])[CH3:21].[NH:43](C(OCC1C2C(=CC=CC=2)C2C1=CC=CC=2)=O)[C@H:44](C(O)=O)[CH2:45][CH2:46][CH2:47][CH2:48][NH:49]C(OC(C)(C)C)=O.C(O)(C(F)(F)F)=O>CCOCC>[NH2:43][C@H:44]([C:26]([NH:18][C@H:19]([C:23]([NH:17][C@H:13]([C:14]([OH:16])=[O:15])[CH2:12][CH2:11][CH2:10][CH2:9][NH2:8])=[O:25])[CH:20]([CH3:21])[CH3:22])=[O:28])[CH2:45][CH2:46][CH2:47][CH2:48][NH2:49]

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 688217FMOC-L-valineHCID 2724628Fmoc-Lys(Boc)-OHHCID 2733283(2S)-2-amino-6-(((tert-butoxy)carbonyl)amino)hexanoic acid

Product 1

HCID 448140Lys-Val-Lys

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

The protective peptide is built on 1.00 g (0.80 mmol) of H-Lys(Boc)-2-chlorotrityl resin using Fmoc-Val-OH, Fmoc-Lys(Boc)-OH and Palm-OSu. The resin is treated for 30 min with 8 ml of TFA 95% and the solution is instilled in 100 ml of Et2O. The precipitate is sucked off, washed and purified by prep. HPLC after drying. The substance is diluted in 30 ml of dioxan:water=4:6, treated overnight with 2.0 g of BioRad resin (acetate form), filtered, rotated and lyophilized. Yield: 110 mg (0.15 mmol, 19%)

Workup

  1. washwashed
  2. custompurified by prep
  3. customHPLC after drying
  4. additionThe substance is diluted in 30 ml of dioxan
  5. additionwater=4:6, treated overnight with 2.0 g of BioRad resin (acetate form)
  6. filtrationfiltered

Sources & evidence

ORD record
ord-73c73a56b2d444b7857252e72f7b484d
Source dataset
uspto-grants-2011_01
Patent number
US07863417B2

Linked notes

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