Benzyl Isothiocyanate → N-(N-(N-(N-L-Tyrosylglycyl)glycyl)-L-phenylalanyl)-L-leucine

HRID 728536Notes

Reaction equation

[CH3:1][CH:2]([CH2:4][CH:5]([NH:9][C:10]([CH:12]([NH:20][C:21]([CH2:23][NH:24][C:25]([CH2:27][NH:28][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:26])=[O:22])[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:11])[C:6]([OH:8])=[O:7])[CH3:3].C(OC(N=C=S)=O)C.C1C=CC(CN=C=S)=CC=1.C(S)[C@@H](O)[C@H](O)CS.N[C@H](C(O)=O)CC(C)C>O>[CH3:3][CH:2]([CH2:4][C@H:5]([NH:9][C:10]([C@@H:12]([NH:20][C:21]([CH2:23][NH:24][C:25]([CH2:27][NH:28][C:29]([C@@H:31]([NH2:40])[CH2:32][C:33]1[CH:38]=[CH:37][C:36]([OH:39])=[CH:35][CH:34]=1)=[O:30])=[O:26])=[O:22])[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:11])[C:6]([OH:8])=[O:7])[CH3:1]

Participants

Conditions

Temperature: 60 °C

Procedure

Immobilized leucine enkephalin (urea linkage) was degraded for two cycles of chemistry. The couplings were performed with ethoxycarbonyl isothiocyanate (instead of BITC) for 5 minutes at 60° C. Cleavages were effected by adding 10 μl of 10% tetra-N-butyl ammonium hydroxide in water containing 1 mg/ml DTT to the dry resin, and heating for 45 minutes at 60° C. Chromatograms are shown in FIGS. 6A and 6B. The cycles were assigned as leucine and phenylalan respectively. The assignments were confirmed by coinjection.

Workup

customfor 5 minutes
customat 60° C

Sources & evidence

ORD record: ord-1901b87bda5e45908163164f4127972f
Source dataset: uspto-grants-1991_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05049507

Reaction notes

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