Water → Ser-Tyr-Ser-Met-Glu-His-Phe-Arg-Tyr-Gly-Lys-Pro-Val-NH2

HRID 1582945Notes

Reaction equation

HRID 1582945 reaction equation
[CH3:1][CH:2]([C@H:4]([NH:8][C:9]([C@H:11]1[N:15]([C:16]([C@@H:18]([NH:24][C:25]([CH2:27][NH:28][C:29]([C@@H:31]([NH:42][C:43]([C@@H:45]([NH:53][C:54]([C@@H:56]([NH:64][C:65]([CH:67]([NH:74][C:75]([C@@H:77]([NH:83][C:84]([C@@H:86]([NH:91][C:92]([C@@H:94]([NH:97][C:98]([C@@H:100]([NH:109][C:110]([C@@H:112]([NH:115]C(C)=O)[CH2:113][OH:114])=[O:111])[CH2:101][C:102]2[CH:107]=[CH:106][C:105]([OH:108])=[CH:104][CH:103]=2)=[O:99])[CH2:95][OH:96])=[O:93])[CH2:87][CH2:88][S:89][CH3:90])=[O:85])[CH2:78][CH2:79][C:80]([OH:82])=[O:81])=[O:76])[CH2:68][C:69]2[NH:73][CH:72]=[N:71][CH:70]=2)=[O:66])[CH2:57][C:58]2[CH:63]=[CH:62][CH:61]=[CH:60][CH:59]=2)=[O:55])[CH2:46][CH2:47][CH2:48][NH:49][C:50]([NH2:52])=[NH:51])=[O:44])[CH2:32]C2C3C(=CC=CC=3)NC=2)=[O:30])=[O:26])[CH2:19][CH2:20][CH2:21][CH2:22][NH2:23])=[O:17])[CH2:14][CH2:13][CH2:12]1)=[O:10])[C:5]([NH2:7])=[O:6])[CH3:3].[OH2:119].C(N([CH2:125][CH3:126])CC)C>C(#N)C>[NH2:115][C@H:112]([C:110]([NH:109][C@H:100]([C:98]([NH:97][C@H:94]([C:92]([NH:91][C@H:86]([C:84]([NH:83][C@H:77]([C:75]([NH:74][C@H:67]([C:65]([NH:64][C@H:56]([C:54]([NH:53][C@H:45]([C:43]([NH:42][C@H:31]([C:29]([NH:28][CH2:27][C:25]([NH:24][C@H:18]([C:16]([N:15]1[CH2:14][CH2:13][CH2:12][C@H:11]1[C:9]([NH:8][C@H:4]([C:5]([NH2:7])=[O:6])[CH:2]([CH3:1])[CH3:3])=[O:10])=[O:17])[CH2:19][CH2:20][CH2:21][CH2:22][NH2:23])=[O:26])=[O:30])[CH2:32][C:126]1[CH:125]=[CH:5][C:4]([OH:119])=[CH:2][CH:1]=1)=[O:44])[CH2:46][CH2:47][CH2:48][NH:49][C:50](=[NH:51])[NH2:52])=[O:55])[CH2:57][C:58]1[CH:63]=[CH:62][CH:61]=[CH:60][CH:59]=1)=[O:66])[CH2:68][C:69]1[N:73]=[CH:72][NH:71][CH:70]=1)=[O:76])[CH2:78][CH2:79][C:80](=[O:81])[OH:82])=[O:85])[CH2:87][CH2:88][S:89][CH3:90])=[O:93])[CH2:95][OH:96])=[O:99])[CH2:101][C:102]1[CH:103]=[CH:104][C:105]([OH:108])=[CH:106][CH:107]=1)=[O:111])[CH2:113][OH:114]

Participants

5

Reactant 3

HCID 962WaterHCID 8471TriethylamineHCID 16129664Czen 002

Product 1

HCID 131724434Ser-Tyr-Ser-Met-Glu-His-Phe-Arg-Tyr-Gly-Lys-Pro-Val-NH2

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

Into 1 ml of stirred solution of 1 mg of α-MSH in a 8:2 mixture of acetonitrile and water placed in a polyethylene test tube under Ar and containing 0.07 mg of triethylamine (TEA), 2.15 mg of NHS-Chlidea (prepared in Example 14a) in a small volume (about 0.2 ml) of acetonitrile was added and shortly sonicated. The reaction mixture, sealed under Ar, was stirred at room temperature in the dark for 66 hrs. In the course of the reaction, aliquots of 15 μl were taken from the reaction mixture, after 0, 3, 19, 45 and 66 hrs from the beginning of the reaction, and were subjected to HPLC analysis.

Workup

  1. customplaced in a polyethylene test tube under Ar
  2. additioncontaining
  3. additionwas added
  4. customshortly sonicated
  5. customThe reaction mixture, sealed under Ar
  6. customIn the course of the reaction, aliquots of 15 μl
  7. customafter 0, 3, 19, 45 and 66 hrs from the beginning of the reaction

Sources & evidence

ORD record
ord-33a414d1929e420e979fc04855215503
Source dataset
uspto-grants-2004_05
Patent number
US06740637B1

Reaction notes

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