Isocyanate → HCID 10326176, compound

HRID 2165710Notes

Reaction equation

HRID 2165710 reaction equation
[NH2:1][C@H:2]([C:11]([OH:13])=O)[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1.[NH2:14][C@H:15]([C:23]([OH:25])=O)[CH2:16][CH2:17][CH2:18][NH:19][C:20](=[NH:22])[NH2:21].[NH2:26][CH2:27][C:28](O)=[O:29].[NH2:31][C@H:32]([C:37]([O-:39])=O)[CH2:33][C:34]([O-:36])=[O:35].[NH2:40][C@H:41]([C:44]([OH:46])=[O:45])[CH2:42][OH:43].[N-]=C=O>P([O-])([O-])([O-])=O.[Na+].[Na+].[Na+].CC(O)C>[CH:5]1[C:4]([CH2:3][C@H:2]([NH2:1])[C:11]([NH:14][C@H:15]([C:23]([NH:26][CH2:27][C:28]([NH:31][C@H:32]([C:37]([NH:40][C@H:41]([C:44]([OH:46])=[O:45])[CH2:42][OH:43])=[O:39])[CH2:33][C:34]([OH:36])=[O:35])=[O:29])=[O:25])[CH2:16][CH2:17][CH2:18][N:19]=[C:20]([NH2:21])[NH2:22])=[O:13])=[CH:9][CH:8]=[C:7]([OH:10])[CH:6]=1

Participants

5

Reactant 2

HCID 105034IsocyanateHCID 178512923HCID 178512923, compound

Product 1

HCID 10326176HCID 10326176, compound

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 24243Trisodium PhosphateSolvent

Procedure

A pentapeptide with a sequence of tyrosine-arginine-glycine-aspartate-serine (single letter code YRGDS) was obtained from Bachem, Inc. The peptide was 98% pure and had a molecular weight of 596.7. A solution of YRGDS was prepared in 0.05M sodium phosphate (pH 7.0), at a concentration of 5.0 mg/ml. To 0.3 ml of the peptide solution was added 30.0 μl of a 200.0 mg/ml solution of Prepolymer F (high temperature) in 2-propanol. These volumes provide a slight excess of peptide (2.51 micromoles) over prepolymer isocyanate (2.4 microequivalents). The mixture was kept at room temperature for 2.5 hours at which time it was analyzed by gel permeation HPLC. The separation system consisted of a Zorbax™ GF250 column (E.I. DuPont de Nemours Co.) and a mobile phase of 0.05M sodium phosphate, 0.3M NaCl (pH 7.0) at a flow rate of 0.5 ml/min. With these conditions, the void and internal volumes were 14.0 minutes (Blue Dextran) and 24.0 minutes (sodium azide), respectively. Peptide-prepolymer conjugate was identified as a broad peak eluting in the 14-20 minute time period. This was clearly separated from unreacted peptide, which eluted at 24 minutes. Free peptide was separated from the bound form using a disposable PD-10 column (Pharmacia).

Sources & evidence

ORD record
ord-882f586eac5b4c119e4a72ba10cc3472
Source dataset
uspto-grants-1990_07
Patent number
US04940737

Reaction notes

Loading…