pGlu-(D)-Ala-Lys(Boc)-Ser-Gln-Gly-(D)-Ala-Ser-Asn-OBut → HCID 131711919, compound

HRID 904041Notes

Reaction equation

HRID 904041 reaction equation
[NH:1]1[C:5](=[O:6])[CH2:4][CH2:3][C@H:2]1[C:7]([NH:9][C@@H:10]([C:12]([NH:14][C@H:15]([C:28]([NH:30][C@H:31]([C:34]([NH:36][C@H:37]([C:43]([NH:45][CH2:46][C:47]([NH:49][C@@H:50]([C:52]([NH:54][C@H:55]([C:58]([NH:60][C@H:61]([C:66]([O:68]C(C)(C)C)=[O:67])[CH2:62][C:63](=[O:65])[NH2:64])=[O:59])[CH2:56][OH:57])=[O:53])[CH3:51])=[O:48])=[O:44])[CH2:38][CH2:39][C:40](=[O:42])[NH2:41])=[O:35])[CH2:32][OH:33])=[O:29])[CH2:16][CH2:17][CH2:18][CH2:19][NH:20]C(OC(C)(C)C)=O)=[O:13])[CH3:11])=[O:8]>FC(F)(F)C(O)=O>[NH:1]1[C:5](=[O:6])[CH2:4][CH2:3][C@H:2]1[C:7]([NH:9][C@@H:10]([C:12]([NH:14][C@H:15]([C:28]([NH:30][C@H:31]([C:34]([NH:36][C@H:37]([C:43]([NH:45][CH2:46][C:47]([NH:49][C@@H:50]([C:52]([NH:54][C@H:55]([C:58]([NH:60][C@H:61]([C:66]([OH:68])=[O:67])[CH2:62][C:63](=[O:65])[NH2:64])=[O:59])[CH2:56][OH:57])=[O:53])[CH3:51])=[O:48])=[O:44])[CH2:38][CH2:39][C:40](=[O:42])[NH2:41])=[O:35])[CH2:32][OH:33])=[O:29])[CH2:16][CH2:17][CH2:18][CH2:19][NH2:20])=[O:13])[CH3:11])=[O:8]

Participants

3

Reactant 1

HCID 131711920pGlu-(D)-Ala-Lys(Boc)-Ser-Gln-Gly-(D)-Ala-Ser-Asn-OBut

Product 1

HCID 131711919HCID 131711919, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

In 2 ml of trifluoroacetic acid is dissolved 250 mg of pGlu-(D)-Ala-Lys(Boc)-Ser-Gln-Gly-(D)-Ala-Ser-Asn-OBut and the solution is allowed to stand at room temperature for 60 minutes. The solvent is distilled off and the residue is precipitated with ether and recovered by filtration. The resulting powders are dissolved in 50 ml of water and passed through a column of Amberlite IRA-410 (acetate-form) (2×5 cm). The effluent is combined with washings and lyophilized. The powdery lyophilizate is dissolved in a small amount of water and put onto a column of Sephadex LH-20 (2.5×125 cm), elution being carried out with 0.1 N-acetic acid. The fractions from 182 ml through 218 ml are pooled and lyophilized. Yield 86 mg (34%); [α]D23 -6.0°(c=0.25, water); Rf4 =0.23; amino acid analysis (as hydrolyzed with HCl): Lys, 0.97(1); Asp, 0.97(1); Ser, 1.80(2); Glu, 2.07(2); Gly, 1.00(1); Ala, 1.93(2); average recovery 82%.

Workup

  1. distillationThe solvent is distilled off
  2. customthe residue is precipitated with ether
  3. filtrationrecovered by filtration
  4. dissolutionThe resulting powders are dissolved in 50 ml of water
  5. dissolutionThe powdery lyophilizate is dissolved in a small amount of water
  6. wash(2.5×125 cm), elution

Sources & evidence

ORD record
ord-2cbee32a21e0447a888ed3580ba800b8
Source dataset
uspto-grants-1980_10
Patent number
US04229438

Reaction notes

Loading…