L-Aspartic Acid → HCID 178448168, compound

HRID 464550Notes

Reaction equation

HRID 464550 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](O)=[O:51])[CH2:42][C:43]1[CH:48]=[CH:47][C:46]([OH:49])=[CH:45][CH:44]=1>>[NH:1]1[C:50](=[O:51])[C@H:41]([CH2:42][C:43]2[CH:48]=[CH:47][C:46]([OH:49])=[CH:45][CH:44]=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

6

Reactant 5

HCID 5960L-Aspartic AcidHCID 5962L-Lysine2×HCID 6057L-TyrosineHCID 6287L-ValineHCID 178418600HCID 178418600, compound2×

Product 1

HCID 178448168HCID 178448168, compound

Procedure

The crude Cyclo-[Arg(Tos)-Lys(Z)-Asp(OBzl)-Val-Tyr(Bzl)] (1 g) was cleaved with 20 ml of HF containing 2 ml anisole at 0° C. for 1 h. The peptide/resin mixture was washed with ether (3×20 ml). The free peptide was extracted with 5 HOAc/H2O (3×20 ml) and lyophilized. The crude material was applied on Sephadex SPC-25 column (60 cm×2.5 cm) previously equilibrated with 0.1M NH4OAc, pH 5. The column was eluted with the equilibration buffer at a flow rate of 85 ml/h and fractions of 13 ml were collected. After 2, the buffer was replaced with 0.2M NH4OAc, pH 6.5. Fractions 201-219 were pooled and lyophilized to give 75 mg of product; Rf, 0.3 (C); Amino acid analysis: acid hydrolysis: Arg, 103; Lys, 1.02; Asp, 1.03; Val, 0.99; Tyr, 0.92; Leucine amino peptidase: traces (<1.7) of Arg and Lys; FAB/MS: MH+ 662; HPLC: C18 -μBondapak column, 10 percent methanol/90 percent 0.02M KH2PO4, pH 3.5, 2 ml/min, 214 nm, elution time 40.67 min.

Workup

  1. washHPLC: C18 -μBondapak column, 10 percent methanol/90 percent 0.02M KH2PO4, pH 3.5, 2 ml/min, 214 nm, elution time 40.67 min.

Sources & evidence

ORD record
ord-d9d98bbe362142deaea18694fd0a69eb
Source dataset
uspto-grants-1985_10
Patent number
US04547489

Reaction notes

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