Ammonia → HCID 100942487, compound

HRID 126795Notes

Reaction equation

HRID 126795 reaction equation
[C:1]([NH:8][C@H:9]([C:14]([OH:16])=O)[CH2:10][CH:11]([CH3:13])[CH3:12])([O:3]C(C)(C)C)=O.[NH2:17][C@H](C(O)=O)CC(C)C.[NH2:26][C@H:27]([C:47]([NH:49][C@@H:50]([C:52]([NH:54][C@H:55](C(N[C@H](C(O)=O)CC(C)C)=O)[CH2:56][C:57]1[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=1)=[O:53])[CH3:51])=[O:48])[CH2:28][C:29]1[CH:34]=[CH:33][C:32]([O:35]C(OCC2C=CC=CC=2Br)=O)=[CH:31][CH:30]=1.N>CO>[NH2:26][C@H:27]([C:47]([NH:49][C@@H:50]([C:52]([NH:54][C@H:55]([C:1]([NH:8][C@H:9]([C:14]([NH2:17])=[O:16])[CH2:10][CH:11]([CH3:12])[CH3:13])=[O:3])[CH2:56][C:57]1[CH:58]=[CH:59][CH:60]=[CH:61][CH:62]=1)=[O:53])[CH3:51])=[O:48])[CH2:28][C:29]1[CH:34]=[CH:33][C:32]([OH:35])=[CH:31][CH:30]=1

Participants

6

Reactant 4

HCID 222AmmoniaHCID 6106L-LeucineHCID 83170L-Leucine, N-((1,1-dimethylethoxy)carbonyl)-HCID 131712099HCID 131712099, compound

Product 1

HCID 100942487HCID 100942487, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Boc-leucine was esterified to chloromethyl polystyrene-1% divinylbenzene in the standard way (cf. Stewart and Young) to give a product containing 0.347 mmoles leucine per gram resin. The peptide sequence was assembled on the resin in the standard way described for Example 1 above, using the Beckman 990 synthesizer. H-Tyr(BrZ)-DAla-Phe-Leu-resin was suspended in anhydrous methanol in a pressure vessel. The solution was chilled to -20°, saturated with ammonia gas, and the vessel was closed and stirred at room temperature for 2 days. Excess ammonia was removed under reduced pressure, the resin was filtered off and discarded, and the peptide solution evaporated to dryness. The blocking group was removed from the tyrosine by treatment with HF-anisole as described in Example 1 above. The peptide was purified by CCD in nBAW (4:1:5); the partition coefficient was 3.0. On paper electrophoresis at pH 5.0 the peptide had Elys =0.50.

Workup

  1. customto give a product
  2. customthe vessel was closed
  3. customExcess ammonia was removed under reduced pressure
  4. filtrationthe resin was filtered off
  5. customthe peptide solution evaporated to dryness
  6. customThe blocking group was removed from the tyrosine by treatment with HF-anisole
  7. customThe peptide was purified by CCD in nBAW (4:1:5)

Sources & evidence

ORD record
ord-a3e59e3a37d44481801874f21b3caa7e
Source dataset
uspto-grants-1981_03
Patent number
US04254024

Reaction notes

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