pGlu-Ala-Lys(Boc)-Ser-Gln-(D)-Ala-Gly-Ser-Asn-OBut → HCID 131711923, compound

HRID 904043Notes

Reaction equation

HRID 904043 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][C@@H:46]([C:48]([NH:50][CH2:51][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])=[O:49])[CH3:47])=[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][C@@H:46]([C:48]([NH:50][CH2:51][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])=[O:49])[CH3:47])=[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 131711924pGlu-Ala-Lys(Boc)-Ser-Gln-(D)-Ala-Gly-Ser-Asn-OBut

Product 1

HCID 131711923HCID 131711923, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

In 5 ml of trifluoroacetic acid is dissolved 500 mg of pGlu-Ala-Lys(Boc)-Ser-Gln-(D)-Ala-Gly-Ser-Asn-OBut and the solution is allowed to stand at room temperature for 40 minutes. The trifluoroacetic acid is distilled off and the residue is precipitated with ether and recovered by filtration. The powdery product is dissolved in 50 ml of water and the solution is 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 0.1 N-acetic acid 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 185 ml through 202 ml are pooled and lyophilized. Yield 170 mg (34%); [α]D27 -50.6° (c=0.42, H2O); Rf4 (Avicel)=0.25; amino acid analysis (acid hydrolyzate); Lys, 1.00(1); Asp, 0.96(1); Ser, 1.77(2), Glu, 2.02(2); Gly, 1.04(1); Ala, 1.95(2); average recovery 75%.

Workup

  1. distillationThe trifluoroacetic acid is distilled off
  2. customthe residue is precipitated with ether
  3. filtrationrecovered by filtration
  4. dissolutionThe powdery product is dissolved in 50 ml of water
  5. dissolutionThe powdery lyophilizate is dissolved in a small amount of 0.1 N-acetic acid
  6. wash(2.5×125 cm), elution

Sources & evidence

ORD record
ord-cc03a65845024b6d9345f509708d1966
Source dataset
uspto-grants-1980_10
Patent number
US04229438

Reaction notes

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