58822-25-6 → HCID 88357735, compound

HRID 1647384Notes

Reaction equation

HRID 1647384 reaction equation
CC(C[CH:5](NC(C(NC(CNC(CN[C:29]([CH:31]([NH2:40])[CH2:32][C:33]1[CH:38]=[CH:37][C:36]([OH:39])=[CH:35][CH:34]=1)=[O:30])=O)=O)CC1C=CC=CC=1)=O)[C:6](O)=[O:7])C.CN(CCCN)C.C(N1C=CN=C1)(N1C=CN=C1)=S.[CH3:60][N:61]([CH2:63][CH2:64][CH2:65][NH:66][C:67]([NH2:69])=[S:68])[CH3:62].FC(F)(F)C(O)=[O:73]>O>[NH2:40][C@H:31]([C:29]([OH:30])=[O:73])[CH2:32][C:33]1[CH:38]=[CH:37][C:36]([OH:39])=[CH:35][CH:34]=1.[CH3:60][N:61]([CH2:63][CH2:64][CH2:65][N:66]1[CH2:5][C:6](=[O:7])[NH:69][C:67]1=[S:68])[CH3:62]

Participants

7

Reactant 5

HCID 390358822-25-63×HCID 6422Trifluoroacetic acid2×HCID 7993N,N-Dimethyl-1,3-propanediamine2×HCID 802641,1'-Thiocarbonyldiimidazole2×HCID 1810294196809-80-0

Product 1

HCID 88357735HCID 88357735, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Reaction of YGGFL with Dimethylaminopropylamine and Thiocarbonyldiimidazole. Dimethylaminopropylamine (1 μmol in 50 μl of DMF) was added to 1,1'-thiocarbonyldiimidazole (1 μmol in 50 μl DMF) and allowed to react for five minutes at 25° C. The pentapeptide, YGGFL (100 nmol in 50 μl DMF), was added and allowed to react for twenty minutes at 25° C. The sample was then taken to dryness in a vacuum centrifuge, redissolved in 0.1% trifluoroacetic acid in water (100 μl), and analyzed by reversed phase HPLC (FIG. 6). The expected peptide product (the N-terminal dimethylaminopropylthiourea derivative; peak B) was identified by FAB/MS (MH+=700) and obtained in approximately 95% yield. Peak A is the starting peptide, YGGFL (MH+=556). Peak B was then treated with 50 μl of anhydrous trifluoroacetic acid for ten minutes at 50° C., dried in a vacuum centrifuge, redissolved in 0.1% trifluoroacetic acid in water (100 μl), and analyzed by reversed phase HPLC. The shortened peptide (GGFL) (MH+=393) and the dimethylaminopropyl thiocarbamyl amino acid (MH+=326) were found in quantitative yield. No dimethylaminopropyl thiohydantoin tyrosine was obtained.

Workup

  1. customto react for five minutes at 25° C
  2. customto react for twenty minutes at 25° C
  3. customobtained in approximately 95% yield
  4. customdried in a vacuum centrifuge
  5. dissolutionredissolved in 0.1% trifluoroacetic acid in water (100 μl)

Sources & evidence

ORD record
ord-afef647ec96542abbe3c6f75cc258067
Source dataset
uspto-grants-1995_07
Patent number
US05432091

Reaction notes

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