L-(+)-Cysteine → Fmoc-Cys(Trt)-Pro

HRID 1289333Notes

Reaction equation

HRID 1289333 reaction equation
[N:1]1([C:9]([O:11][CH2:12][CH:13]2[C:25]3C(=CC=C[CH:24]=3)[C:19]3[C:14]2=[CH:15][CH:16]=[CH:17][CH:18]=3)=[O:10])[CH2:8][CH2:7]C[C@H]1C(O)=O.C(O[C:34]1[CH:41]=[CH:40][C:37]([CH2:38]O)=[CH:36][CH:35]=1)C1C=CC=CC=1.[NH:42]1[CH2:49][CH2:48][CH2:47][C@H:43]1[C:44]([OH:46])=[O:45].C1CN(C(OCC2[C:71]3[C:66](=[CH:67][CH:68]=[CH:69][CH:70]=3)C3C2=CC=CC=3)=O)[C@H](C=O)C1.N1C[CH2:78][CH2:77][CH2:76][CH2:75]1.CN(C=O)C.N[C@H](C(O)=O)[CH2:87][SH:88].C1CCC(N=C=N[CH:101]2[CH2:106][CH2:105][CH2:104][CH2:103][CH2:102]2)CC1.C1C=CC2N([OH:116])N=NC=2C=1>ClCCl>[NH:1]([C:9]([O:11][CH2:12][CH:13]1[C:25]2[C:24](=[CH:75][CH:76]=[CH:77][CH:78]=2)[C:15]2[C:14]1=[CH:19][CH:18]=[CH:17][CH:16]=2)=[O:10])[C@H:8]([C:7]([N:42]1[CH2:49][CH2:48][CH2:47][C@H:43]1[C:44]([OH:46])=[O:45])=[O:116])[CH2:87][S:88][C:38]([C:37]1[CH:36]=[CH:35][CH:34]=[CH:41][CH:40]=1)([C:66]1[CH:67]=[CH:68][CH:69]=[CH:70][CH:71]=1)[C:101]1[CH:102]=[CH:103][CH:104]=[CH:105][CH:106]=1

Participants

9

Reactant 7

HCID 5862L-(+)-CysteineHCID 70043(4-(Benzyloxy)phenyl)methanolHCID 145742L-ProlineHCID 688135Fmoc-Pro-OHHCID 11290200Fmoc-Pro-Wang resinHCID 21712060DCCI HOBtHCID 23501187piperidine N,N-dimethylformamide

Product 1

HCID 131720636Fmoc-Cys(Trt)-Pro

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

0.6 g of Fmoc-Pro-OH is dissolved in 100 ml of dichloromethane, 1.2 equivalents of Wang resin (p-benzyloxybenzyl alcohol resin) are added, and the mixture is stirred at room temperature for 12 hours. After removal of the solvent Fmoc-Pro-Wang resin is obtained. In a peptide synthesizer Fmoc-Cys(Trt)-OH is condensed with H-Pro-Wang resin [liberation from Fmoc-Pro-Wang resin using piperidine/DMF (20% strength)], using a three-fold excess of the protected cysteine. The coupling is carried out at room temperature in DCCI/HOBt, to give Fmoc-Cys(Trt)-Pro-Wang resin. Subsequent treatment with piperidine/DMF (20% strength) again gives H-Cys(Trt)-Pro-Wang resin.

Workup

  1. customAfter removal of the solvent Fmoc-Pro-Wang resin
  2. customis obtained

Sources & evidence

ORD record
ord-38c117d6d4854ea7ad460c44f7245cf8
Source dataset
uspto-grants-1998_05
Patent number
US05747457

Reaction notes

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