HCID 131711780, compound → H-ALA-GLN-ASP-PHE-VAL-GLN-TRP-LEU-MET-ASN-THR-OH

HRID 1706294Notes

Reaction equation

HRID 1706294 reaction equation
[NH2:1][C@H:2]([C:4]([NH:6][C@H:7]([C:13]([NH:15][C@H:16]([C:21]([NH:23][C@H:24]([C:32]([NH:34][C@H:35]([C:39]([NH:41][C@H:42]([C:48]([NH:50][C@H:51]([C:62]([NH:64][C@H:65]([C:70]([NH:72][C@H:73]([C:79]([NH:81][C@H:82]([C:87]([NH:89][C@H:90]([C:94]([OH:96])=[O:95])[C@@H:91]([CH3:93])[OH:92])=[O:88])[CH2:83][C:84](=[O:86])[NH2:85])=[O:80])[CH2:74][CH2:75][S:76]([CH3:78])=O)=[O:71])[CH2:66][CH:67]([CH3:69])[CH3:68])=[O:63])[CH2:52][C:53]1[C:61]2[C:56](=[CH:57][CH:58]=[CH:59][CH:60]=2)[NH:55][CH:54]=1)=[O:49])[CH2:43][CH2:44][C:45](=[O:47])[NH2:46])=[O:40])[CH:36]([CH3:38])[CH3:37])=[O:33])[CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[O:22])[CH2:17][C:18](=[O:20])[OH:19])=[O:14])[CH2:8][CH2:9][C:10](=[O:12])[NH2:11])=[O:5])[CH3:3]>C(O)(=O)CS>[NH2:1][C@H:2]([C:4]([NH:6][C@H:7]([C:13]([NH:15][C@H:16]([C:21]([NH:23][C@H:24]([C:32]([NH:34][C@H:35]([C:39]([NH:41][C@H:42]([C:48]([NH:50][C@H:51]([C:62]([NH:64][C@H:65]([C:70]([NH:72][C@H:73]([C:79]([NH:81][C@H:82]([C:87]([NH:89][C@H:90]([C:94]([OH:96])=[O:95])[C@@H:91]([CH3:93])[OH:92])=[O:88])[CH2:83][C:84](=[O:86])[NH2:85])=[O:80])[CH2:74][CH2:75][S:76][CH3:78])=[O:71])[CH2:66][CH:67]([CH3:69])[CH3:68])=[O:63])[CH2:52][C:53]1[C:61]2[C:56](=[CH:57][CH:58]=[CH:59][CH:60]=2)[NH:55][CH:54]=1)=[O:49])[CH2:43][CH2:44][C:45](=[O:47])[NH2:46])=[O:40])[CH:36]([CH3:37])[CH3:38])=[O:33])[CH2:25][C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1)=[O:22])[CH2:17][C:18](=[O:19])[OH:20])=[O:14])[CH2:8][CH2:9][C:10](=[O:12])[NH2:11])=[O:5])[CH3:3]

Participants

3

Reactant 1

HCID 131711780HCID 131711780, compound

Product 1

HCID 3080901H-ALA-GLN-ASP-PHE-VAL-GLN-TRP-LEU-MET-ASN-THR-OH

Reagents, catalysts & solvents 1

HCID 1133Thioglycolic AcidSolvent

Procedure

In 3.0 ml of 5% thioglycolic acid-50% aqueous acetic acid was dissolved 30 mg of H-Ala-Gln-Asp-Phe-Val-Gln-Trp-Leu-Met(O)-Asn-Thr-OH and reduction was carried out at 45° C. for 24 hours. The reaction mixture was run onto a column (3.4×57 cm) of Sephadex LH-20 and elution was carried out with 50% acetic acid. The fractions from 235 ml to 280 ml were pooled and lyophilized. Yield 23 mg; Rf3 0.72(Avicel®); amino acid analysis; Trp (0.76(1); Asp 2.15(2); Thr 0.93(1); Glu 2.15(2); Ala 0.97(1); Val 1.00(1); Met 0.92(1); Leu 1.02 (1); Phe 1.02(1) (peptide content 82%)

Workup

  1. washand elution

Sources & evidence

ORD record
ord-ca24aadc652c4cbcac684a9bbffdfa83
Source dataset
uspto-grants-1980_06
Patent number
US04206199

Reaction notes

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