Acetic Acid → HCID 178476580, compound

HRID 1154156Notes

Reaction equation

HRID 1154156 reaction equation
[NH:1](C(OCC1C=CC=CC=1)=O)[C@H:2]([C:8]([NH:10][C@H:11]([C:17]([NH:19][C@H:20]([C:29]([NH:31][C@H:32]([C:40]([NH:42][C@H:43]([C:51]([OH:53])=[O:52])[CH2:44][CH2:45][CH2:46][NH:47][C:48](=[NH:50])[NH2:49])=[O:41])[CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)=[O:30])[CH2:21][C:22]1[CH:27]=[CH:26][C:25]([OH:28])=[CH:24][CH:23]=1)=[O:18])[CH2:12][CH2:13][CH2:14][CH2:15][NH2:16])=[O:9])[CH2:3][CH2:4][CH2:5][CH2:6][NH2:7].CC(O)=O.CC(O)=O.N[C@H](C(O)=O)CC1C=CC(O)=CC=1.N[C@H](C(O)=O)CC1C=CC=CC=1.N[C@H](C(O)=O)CCCCN.N[C@H](C(O)=O)CCCNC(=N)N.C(O)(=O)C>>[NH2:1][C@H:2]([C:8]([NH:10][C@H:11]([C:17]([NH:19][C@H:20]([C:29]([NH:31][C@H:32]([C:40]([NH:42][C@H:43]([C:51]([OH:53])=[O:52])[CH2:44][CH2:45][CH2:46][NH:47][C:48](=[NH:49])[NH2:50])=[O:41])[CH2:33][C:34]1[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=1)=[O:30])[CH2:21][C:22]1[CH:27]=[CH:26][C:25]([OH:28])=[CH:24][CH:23]=1)=[O:18])[CH2:12][CH2:13][CH2:14][CH2:15][NH2:16])=[O:9])[CH2:3][CH2:4][CH2:5][CH2:6][NH2:7].[CH3:43][C:51]([OH:53])=[O:52].[CH3:43][C:51]([OH:53])=[O:52]

Participants

7

Reactant 6

HCID 176Acetic AcidHCID 5962L-LysineHCID 6057L-TyrosineHCID 6140L-PhenylalanineHCID 178418600HCID 178418600, compoundHCID 178476579HCID 178476579, compound

Product 1

HCID 178476580HCID 178476580, compound

Procedure

500 mg of Z-Lys-Lys-Tyr-Phe-Arg diacetate are dissolved in 20 ml of 90% strength acetic acid and subjected to catalytic hydrogenation analogously to Example 1 h. The residue is chromatographed in 90% strength methanol over a crosslinked, hydroxypropylated dextran gel. The eluate containing the peptide is concentrated and the residue is dissolved in water and freeze-dried. Yield 244 mg. Aminoacid analysis (hydrolysis in 6N HCl for 24 hours at 120° C.): Tyr 0.93, Phe 1.0, Lys 2.06 and Arg. 0.9.

Workup

  1. customsubjected to catalytic hydrogenation analogously to Example 1 h
  2. customThe residue is chromatographed in 90% strength methanol over a crosslinked, hydroxypropylated dextran gel
  3. additionThe eluate containing the peptide
  4. concentrationis concentrated
  5. dissolutionthe residue is dissolved in water
  6. customfreeze-dried
  7. customAminoacid analysis (hydrolysis in 6N HCl for 24 hours at 120° C.)

Sources & evidence

ORD record
ord-26c00600fc3141129d58833c5d1d5f94
Source dataset
uspto-grants-1984_12
Patent number
US04487764

Reaction notes

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