HCID 178445960, compound → HCID 178503705, compound

HRID 1706292Notes

Reaction equation

HRID 1706292 reaction equation
[NH2:1][C@H:2]([C:10]([NH:12][C@H:13]([C:15]([NH:17][C@H:18]([C:24]([NH:26][C@H:27]([C:32]([NH:34][C@H:35]([C:43]([NH:45][C@H:46]([C:50]([NH:52][C@H:53]([C:59]([NH:61][C@H:62]([C:73]([NH:75][C@H:76]([C:81]([NH:83][C@H:84]([C:90]([NH:92][C@H:93]([C:98]([NH:100][C@H:101]([C:105]([OH:107])=[O:106])[C@@H:102]([CH3:104])[OH:103])=[O:99])[CH2:94][C:95](=[O:97])[NH2:96])=[O:91])[CH2:85][CH2:86][S:87]([CH3:89])=O)=[O:82])[CH2:77][CH:78]([CH3:80])[CH3:79])=[O:74])[CH2:63][C:64]1[C:72]2[C:67](=[CH:68][CH:69]=[CH:70][CH:71]=2)[NH:66][CH:65]=1)=[O:60])[CH2:54][CH2:55][C:56](=[O:58])[NH2:57])=[O:51])[CH:47]([CH3:49])[CH3:48])=[O:44])[CH2:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)=[O:33])[CH2:28][C:29](=[O:31])[OH:30])=[O:25])[CH2:19][CH2:20][C:21](=[O:23])[NH2:22])=[O:16])[CH3:14])=[O:11])[CH2:3][CH2:4][CH2:5][NH:6][C:7](=[NH:9])[NH2:8]>C(O)(=O)CS>[NH2:1][C@H:2]([C:10]([NH:12][C@H:13]([C:15]([NH:17][C@H:18]([C:24]([NH:26][C@H:27]([C:32]([NH:34][C@H:35]([C:43]([NH:45][C@H:46]([C:50]([NH:52][C@H:53]([C:59]([NH:61][C@H:62]([C:73]([NH:75][C@H:76]([C:81]([NH:83][C@H:84]([C:90]([NH:92][C@H:93]([C:98]([NH:100][C@H:101]([C:105]([OH:107])=[O:106])[C@@H:102]([CH3:104])[OH:103])=[O:99])[CH2:94][C:95](=[O:97])[NH2:96])=[O:91])[CH2:85][CH2:86][S:87][CH3:89])=[O:82])[CH2:77][CH:78]([CH3:80])[CH3:79])=[O:74])[CH2:63][C:64]1[C:72]2[C:67](=[CH:68][CH:69]=[CH:70][CH:71]=2)[NH:66][CH:65]=1)=[O:60])[CH2:54][CH2:55][C:56](=[O:58])[NH2:57])=[O:51])[CH:47]([CH3:48])[CH3:49])=[O:44])[CH2:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)=[O:33])[CH2:28][C:29](=[O:30])[OH:31])=[O:25])[CH2:19][CH2:20][C:21](=[O:23])[NH2:22])=[O:16])[CH3:14])=[O:11])[CH2:3][CH2:4][CH2:5][NH:6][C:7](=[NH:8])[NH2:9]

Participants

3

Reactant 1

HCID 178445960HCID 178445960, compound

Product 1

HCID 178503705HCID 178503705, compound

Reagents, catalysts & solvents 1

HCID 1133Thioglycolic AcidSolvent

Procedure

In 2.5 ml of 5% thioglycolic acid-50% aqueous acetic acid was dissolved 25 mg of H-Arg-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 30% aqueous acetic acid. The fractions from 200 ml to 240 ml were pooled and lyophilized. Yield 20 mg; Rf3 0.62 (Avicel®); amino acid analysis: Trp 0.74(1); Arg 1.13(1); Asp 2.08(2); Thr 0.95(1); Glu 2.03(2); Ala 1.00(1); Val 0.98(1); Met 0.93(1); Leu 0.99(1); Phe 0.98(1) (peptide content 79%)

Workup

  1. washand elution

Sources & evidence

ORD record
ord-2999c9f3d2ad46fda6f625e40b52fdeb
Source dataset
uspto-grants-1980_06
Patent number
US04206199

Reaction notes

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