Phenacylamine → Phenacylamine

HRID 1625689Notes

Reaction equation

HRID 1625689 reaction equation
[NH2:1][CH2:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:4].[NH2:11][C:12]1[CH:25]=[CH:24][C:23]([N+]([O-])=O)=[CH:22][C:13]=1[C:14](C1C=CC=CC=1)=[O:15]>C([O-])(=O)C.[Na+]>[NH2:11][C:12]1[CH:25]=[CH:24][CH:23]=[CH:22][C:13]=1[CH:14]=[O:15].[NH2:1][CH2:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:4]

Participants

5

Reactant 2

HCID 11952PhenacylamineHCID 156812-Amino-5-nitrobenzophenone

Product 2

HCID 11952PhenacylamineHCID 682552-Aminobenzaldehyde

Reagents, catalysts & solvents 1

HCID 517045Sodium AcetateSolvent

Procedure

Evaluation of the reaction efficiency as a function of the reactant to protein concentration ratio, and the reactivity with 2-ABA-like reactants is shown in FIG. 27. The mass spectra of hRBP4 with PCL incorporated at position 122 (hRBP4 Phe122PCL) after reaction with 0.1 mM 2-amino-benzaldehyde (2-ABA) is shown in FIG. 27A, while the mass spectra for hRBP4 Phe122PCL after reaction with 0.1 mM 2-amino-acetophenone (2-AAP) and 0.1 mM 2-amino-5-nitro-benzophenone (2-ANBP) are shown if FIG. 27B and FIG. 27C, respectively. All reactions were performed in 200 mM sodium acetate, pH 5.0. The protein conjugates are detected at the correct mass and with the expected mass increase as given in FIG. 23. In addition, yields of greater than 88% conversion for 2-ABA and 2-AAP were achieved, although because of low solubility a yield of about 5% was obtained for 2-ANBP. However, this demonstrates that 2-ABA analogues react efficiently at the PCL incorporation site at reactant to protein concentration ratios of 6 to 1. The extent of the reactions is only slightly lower than those performed at reactant to protein ratios of 600 to 1 (FIG. 26).

Workup

  1. concentrationEvaluation of the reaction efficiency as a function of the reactant to protein concentration ratio
  2. customThe mass spectra of hRBP4 with PCL incorporated at position 122 (hRBP4 Phe122PCL) after reaction with 0.1 mM 2-amino-benzaldehyde (2-ABA)
  3. temperaturewith the expected mass increase

Sources & evidence

ORD record
ord-360df24fabcb4331977d2a2e7e11b5ba
Source dataset
uspto-grants-2014_07
Patent number
US08785151B2

Reaction notes

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