HRID1827259

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID750

Glycine

C2H5NO2

HCID71567

D-Phenylalanine

C9H11NO2

HCID444080

N-Methyl-L-valine

C6H13NO2

HCID7010570

4-tert-Butyl hydrogen L-aspartate

C8H15NO4

HCID21863450

未命名化合物

结构：COc1cc(C)c(S(=O)(=O)NC(=N)NCCC[C@H](NC(=O)OCC2c3ccccc3-c3ccccc32)C(=O)NCC(=O)N[C@@H](CC(=O)OC(C)(C)C)C(=O)N[C@H](Cc2ccccc2)C(=O)N(C)[C@H](C(=O)O[Na])C(C)C)c(C)c1C

HCID178491778

未命名化合物

结构：COc1cc(C)c(S(=O)(=O)NC(=N)NCCC[C@H](NC(=O)OCC2c3ccccc3-c3ccccc32)C(=O)O)c(C)c1C

HCID178491779

未命名化合物

PRODUCTS

生成物

结构：COc1cc(C)c(S(=O)(=O)NC(=N)NCCC[C@H](NC(=O)OCC2c3ccccc3-c3ccccc32)C(=O)NCC(=O)N[C@@H](CC(=O)OC(C)(C)C)C(=O)N[C@H](Cc2ccccc2)C(=O)N(C)[C@H](C(=O)O)C(C)C)c(C)c1C

HCID178491777

未命名化合物

PROCEDURE

实验过程

Fmoc-Arg(Mtr)-Gly-Asp(OBut)-DPhe-NMeVal-ONa (SEQ ID NO 41) is synthesized using solid-phase Merrifield-type procedures by sequentially adding NMeVal, DPhe, Asp(OBut), Gly and Fmoc-Arg(Mtr) in a step-wise manner to a 4-hydroxymethyl-phenoxymethyl-polystyrene resin (Wang type resin) (customary Merrifield-type methods of peptide synthesis are applied as described in Houben-Weyl, l.c., Volume 15/II, Pages 1 to 806 (1974). The polystyrene resin and amino acid residues precursors are commercially available from Aldrich, Sigma or Fluka chemical companies). After completion of sequential addition of the amino acid residues, the resin is then eliminated from the peptide chain using a 1:1 mixture of TFA/dichloromethane which provides the Fmoc-Arg(Mtr)-Gly-Asp(OBut)-DPhe-NMeVal-OH product (SEQ ID NO 42). The Fmoc group is then removed with a 1:1 mixture of piperidine/DMF which provides the crude Arg(Mtr)-Gly-Asp(OBut)-DPhe-NMeVal-OH (SEQ ID NO 43) precursor which is then purified by HPLC in the customary manner.

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-8a1f3e9205a64558bb261b5185b2c6ca
来源数据集: uspto-grants-2006_05
DOI: 10.6084/m9.figshare.5104873.v1
专利: US07053041B1
来源说明: uspto-grants-2006_05

反应 SMILES

[NH:1]([C:63]([O:65][CH2:66][CH:67]1[C:79]2[C:74](=[CH:75][CH:76]=[CH:77][CH:78]=2)[C:73]2[C:68]1=[CH:69][CH:70]=[CH:71][CH:72]=2)=[O:64])[C@H:2]([C:24]([NH:26][CH2:27][C:28]([NH:30][C@H:31]([C:40]([NH:42][C@@H:43]([C:51]([N:53]([CH3:62])[C@H:54]([C:58]([O:60][Na])=[O:59])[CH:55]([CH3:57])[CH3:56])=[O:52])[CH2:44][C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1)=[O:41])[CH2:32][C:33](=[O:39])[O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:29])=[O:25])[CH2:3][CH2:4][CH2:5][NH:6][C:7](=[NH:23])[NH:8][S:9]([C:12]1[C:21]([CH3:22])=[C:19]([CH3:20])[C:16]([O:17][CH3:18])=[CH:15][C:13]=1[CH3:14])(=[O:11])=[O:10].N(C)[C@H](C(O)=O)C(C)C.N[C@@H](C(O)=O)CC1C=CC=CC=1.N[C@H](C(O)=O)CC(=O)OC(C)(C)C.NCC(O)=O.N(C(OCC1C2C(=CC=CC=2)C2C1=CC=CC=2)=O)[C@H](C(O)=O)CCCNC(=N)NS(C1C(C)=C(C)C(OC)=CC=1C)(=O)=O.C(O)(C(F)(F)F)=O.ClCCl>>[NH:1]([C:63]([O:65][CH2:66][CH:67]1[C:79]2[C:74](=[CH:75][CH:76]=[CH:77][CH:78]=2)[C:73]2[C:68]1=[CH:69][CH:70]=[CH:71][CH:72]=2)=[O:64])[C@H:2]([C:24]([NH:26][CH2:27][C:28]([NH:30][C@H:31]([C:40]([NH:42][C@@H:43]([C:51]([N:53]([CH3:62])[C@H:54]([C:58]([OH:60])=[O:59])[CH:55]([CH3:56])[CH3:57])=[O:52])[CH2:44][C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1)=[O:41])[CH2:32][C:33](=[O:39])[O:34][C:35]([CH3:38])([CH3:36])[CH3:37])=[O:29])=[O:25])[CH2:3][CH2:4][CH2:5][NH:6][C:7](=[NH:23])[NH:8][S:9]([C:12]1[C:21]([CH3:22])=[C:19]([CH3:20])[C:16]([O:17][CH3:18])=[CH:15][C:13]=1[CH3:14])(=[O:11])=[O:10]