HCID 131711777, compound → HCID 131711776, compound

HRID 1706291Notes

Reaction equation

HRID 1706291 reaction equation
[NH2:1][C@H:2]([C:10]([NH:12][C@H:13]([C:21]([NH:23][C@H:24]([C:26]([NH:28][C@H:29]([C:35]([NH:37][C@H:38]([C:43]([NH:45][C@H:46]([C:54]([NH:56][C@H:57]([C:61]([NH:63][C@H:64]([C:70]([NH:72][C@H:73]([C:84]([NH:86][C@H:87]([C:92]([NH:94][C@H:95]([C:101]([NH:103][C@H:104]([C:109]([NH:111][C@H:112]([C:116]([OH:118])=[O:117])[C@@H:113]([CH3:115])[OH:114])=[O:110])[CH2:105][C:106](=[O:108])[NH2:107])=[O:102])[CH2:96][CH2:97][S:98]([CH3:100])=O)=[O:93])[CH2:88][CH:89]([CH3:91])[CH3:90])=[O:85])[CH2:74][C:75]1[C:83]2[C:78](=[CH:79][CH:80]=[CH:81][CH:82]=2)[NH:77][CH:76]=1)=[O:71])[CH2:65][CH2:66][C:67](=[O:69])[NH2:68])=[O:62])[CH:58]([CH3:60])[CH3:59])=[O:55])[CH2:47][C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1)=[O:44])[CH2:39][C:40](=[O:42])[OH:41])=[O:36])[CH2:30][CH2:31][C:32](=[O:34])[NH2:33])=[O:27])[CH3:25])=[O:22])[CH2:14][CH2:15][CH2:16][NH:17][C:18](=[NH:20])[NH2:19])=[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:21]([NH:23][C@H:24]([C:26]([NH:28][C@H:29]([C:35]([NH:37][C@H:38]([C:43]([NH:45][C@H:46]([C:54]([NH:56][C@H:57]([C:61]([NH:63][C@H:64]([C:70]([NH:72][C@H:73]([C:84]([NH:86][C@H:87]([C:92]([NH:94][C@H:95]([C:101]([NH:103][C@H:104]([C:109]([NH:111][C@H:112]([C:116]([OH:118])=[O:117])[C@@H:113]([CH3:115])[OH:114])=[O:110])[CH2:105][C:106](=[O:108])[NH2:107])=[O:102])[CH2:96][CH2:97][S:98][CH3:100])=[O:93])[CH2:88][CH:89]([CH3:90])[CH3:91])=[O:85])[CH2:74][C:75]1[C:83]2[C:78](=[CH:79][CH:80]=[CH:81][CH:82]=2)[NH:77][CH:76]=1)=[O:71])[CH2:65][CH2:66][C:67](=[O:69])[NH2:68])=[O:62])[CH:58]([CH3:60])[CH3:59])=[O:55])[CH2:47][C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1)=[O:44])[CH2:39][C:40](=[O:41])[OH:42])=[O:36])[CH2:30][CH2:31][C:32](=[O:34])[NH2:33])=[O:27])[CH3:25])=[O:22])[CH2:14][CH2:15][CH2:16][NH:17][C:18](=[NH:19])[NH2:20])=[O:11])[CH2:3][CH2:4][CH2:5][NH:6][C:7](=[NH:8])[NH2:9]

Participants

3

Reactant 1

HCID 131711777HCID 131711777, compound

Product 1

HCID 131711776HCID 131711776, compound

Reagents, catalysts & solvents 1

HCID 1133Thioglycolic AcidSolvent

Procedure

In 3 ml of 5% thioglycolic acid-50% aqueous acetic acid was dissolved 30 mg of H-Arg-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. Then, the reaction mixture was run onto a column (2.4×122 cm) of Sephadex G-25 and elution was carried out with 30% aqueous acetic acid. The fractions from 180 ml to 250 ml were pooled and lyophilized. Yield 29 mg; [α]D21 -41.9° (c=0.4%, 0.1 N-HCl); Rf3 0.55(Avicel®); amino acid analysis: Trp 0.69(1); Arg 2.25(2); Asp 2.13(2); Thr 0.97(1); Glu 2.16(2); Ala 1.00(1); Val 1.01(1); Met 0.97(1); Leu 1.01(1); Phe 1.05(1); (peptide content 78%)

Workup

  1. washand elution

Sources & evidence

ORD record
ord-cebb3fb724834ffa9df1c8d4d7883840
Source dataset
uspto-grants-1980_06
Patent number
US04206199

Reaction notes

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