Fmoc-Lys(Boc)-Thr(But)-Ala-Asn(Trt)-OH → Fmoc-Lys(Boc)-Thr(But)-Ala-Asn(Trt)-Cys(Trt)-Pro

HRID 1289334Notes

Reaction equation

HRID 1289334 reaction equation
[NH2:1][C@H:2]([C:24]([N:26]1[CH2:33][CH2:32][CH2:31][C@H:27]1[C:28]([OH:30])=[O:29])=[O:25])[CH2:3][S:4][C:5]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[NH:34]([C:94]([O:96][CH2:97][CH:98]1[C:110]2[C:105](=[CH:106][CH:107]=[CH:108][CH:109]=2)[C:104]2[C:99]1=[CH:100][CH:101]=[CH:102][CH:103]=2)=[O:95])[C@H:35]([C:48]([NH:50][C@H:51]([C:59]([NH:61][C@H:62]([C:64]([NH:66][C@H:67]([C:91](O)=[O:92])[CH2:68][C:69](=[O:90])[NH:70][C:71]([C:84]1[CH:89]=[CH:88][CH:87]=[CH:86][CH:85]=1)([C:78]1[CH:83]=[CH:82][CH:81]=[CH:80][CH:79]=1)[C:72]1[CH:77]=[CH:76][CH:75]=[CH:74][CH:73]=1)=[O:65])[CH3:63])=[O:60])[C@@H:52]([CH3:58])[O:53][C:54]([CH3:57])([CH3:56])[CH3:55])=[O:49])[CH2:36][CH2:37][CH2:38][CH2:39][NH:40][C:41]([O:43][C:44]([CH3:47])([CH3:46])[CH3:45])=[O:42]>C1CCC(N=C=NC2CCCCC2)CC1.C1C=CC2N(O)N=NC=2C=1>[NH:34]([C:94]([O:96][CH2:97][CH:98]1[C:110]2[C:105](=[CH:106][CH:107]=[CH:108][CH:109]=2)[C:104]2[C:99]1=[CH:100][CH:101]=[CH:102][CH:103]=2)=[O:95])[C@H:35]([C:48]([NH:50][C@H:51]([C:59]([NH:61][C@H:62]([C:64]([NH:66][C@H:67]([C:91]([NH:1][C@H:2]([C:24]([N:26]1[CH2:33][CH2:32][CH2:31][C@H:27]1[C:28]([OH:30])=[O:29])=[O:25])[CH2:3][S:4][C:5]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)([C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)[C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1)=[O:92])[CH2:68][C:69](=[O:90])[NH:70][C:71]([C:78]1[CH:83]=[CH:82][CH:81]=[CH:80][CH:79]=1)([C:84]1[CH:85]=[CH:86][CH:87]=[CH:88][CH:89]=1)[C:72]1[CH:73]=[CH:74][CH:75]=[CH:76][CH:77]=1)=[O:65])[CH3:63])=[O:60])[C@@H:52]([CH3:58])[O:53][C:54]([CH3:57])([CH3:55])[CH3:56])=[O:49])[CH2:36][CH2:37][CH2:38][CH2:39][NH:40][C:41]([O:43][C:44]([CH3:45])([CH3:46])[CH3:47])=[O:42]

Participants

4

Reactant 2

HCID 15780746Fmoc-Lys(Boc)-Thr(But)-Ala-Asn(Trt)-OHHCID 131720638H-Cys(Trt)-Pro

Product 1

HCID 131720637Fmoc-Lys(Boc)-Thr(But)-Ala-Asn(Trt)-Cys(Trt)-Pro

Reagents, catalysts & solvents 1

HCID 21712060DCCI HOBtSolvent

Procedure

0.4 g of H-Cys(Trt)-Pro-Wang resin are condensed in a peptide synthesizer (continuous flow principle) with Fmoc-Lys(Boc)-Thr(But)-Ala-Asn(Trt)-OH (SEQ ID NO:87), using a three-fold excess of the Fmoc peptide. The coupling is carried out at room temperature in DCCI/HOBt, to give Fmoc-Lys(Boc)-Thr(But)-Ala-Asn(Trt)-Cys(Trt)-Pro-Wang (SEQ ID NO:223) resin. Subsequent treatment with TFA/CH2Cl2 followed by removal of the Fmoc group with piperidine/DMF (20%) gives H-Lys-Thr-Ala-Asn-Cys(Trt)-Pro-OH (SEQ ID NO:92).

Sources & evidence

ORD record
ord-7ba4f0bc0934468bb14c5489ada296e4
Source dataset
uspto-grants-1998_05
Patent number
US05747457

Reaction notes

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