Glycine → HCID 178448169, compound

HRID 464551Notes

Reaction equation

HRID 464551 reaction equation
[NH2:1][C@H:2]([C:10]([OH:12])=O)[CH2:3][CH2:4][CH2:5][NH:6][C:7](=[NH:9])[NH2:8].[NH2:13][C@H:14]([C:20]([OH:22])=O)[CH2:15][CH2:16][CH2:17][CH2:18][NH2:19].[NH2:23][C@H:24]([C:29]([OH:31])=O)[CH2:25][C:26](=[O:28])[OH:27].[NH2:32][C@H:33]([C:37]([OH:39])=O)[CH:34]([CH3:36])[CH3:35].[NH2:40][C@H:41]([C:50]([OH:52])=O)[CH2:42][C:43]1[CH:48]=[CH:47][C:46]([OH:49])=[CH:45][CH:44]=1.[NH2:53][CH2:54][C:55](O)=[O:56]>CO>[NH:1]1[C:55](=[O:56])[CH2:54][NH:53][C:50](=[O:52])[C@H:41]([CH2:42][C:43]2[CH:44]=[CH:45][C:46]([OH:49])=[CH:47][CH:48]=2)[NH:40][C:37](=[O:39])[C@H:33]([CH:34]([CH3:36])[CH3:35])[NH:32][C:29](=[O:31])[C@H:24]([CH2:25][C:26](=[O:28])[OH:27])[NH:23][C:20](=[O:22])[C@H:14]([CH2:15][CH2:16][CH2:17][CH2:18][NH2:19])[NH:13][C:10](=[O:12])[C@@H:2]1[CH2:3][CH2:4][CH2:5][NH:6][C:7](=[NH:9])[NH2:8]

Participants

8

Reactant 6

HCID 750Glycine2×HCID 5960L-Aspartic AcidHCID 5962L-LysineHCID 6057L-Tyrosine2×HCID 6287L-ValineHCID 178418600HCID 178418600, compound

Product 1

HCID 178448169HCID 178448169, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The crude cyclo[Arg(Tos)-Lys(Z)-Asp(OBzl)-Val-Tyr(Bzl)-Gly] (1 g) was cleaved with HF/anisole (20 ml; 9:1) at 0° C. for 1 h. The peptide resin mixture was washed with diethylether (3×20 ml). The peptide was extracted with 5 aqueous acetic acid (3×20 ml) and lyophilized. The crude material was chromatographed on a Sephadex SPC-25 column (60 cm×2.5 cm), equilibrated with 0.2M NH OAc, pH 5.25 at a flow rate of 85 ml/h with a fraction size of 10 ml. Fractions 130-153 were pooled and lyophilized to give 40 mg of material; Rf 0.32 (C); Amino acid analysis: Acid hydrolysis: Arg, 1.02; Lys, 0.98; Asp, 1.08; Val, 1.03; Tyr, 0.93; Gly, 0.95; Carboxypeptidase A hydrolysis: trace (<3 percent) of Tyr and Gly; FAB/MS MH+ =719; HPLC: C18 -μBondapak, 2 ml/min, 214 nm, 10 percent methanol/0.02M KH2PO4, pH 3.5, retention time 60.26 min.

Workup

  1. customCarboxypeptidase A hydrolysis

Sources & evidence

ORD record
ord-1954a98fe0894c0f8a5855d34e4f419b
Source dataset
uspto-grants-1985_10
Patent number
US04547489

Reaction notes

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