Glycine → HCID 178491777, compound

HRID 1827259

Reaction equation

[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]

Participants

Reactant 7

HCID 750Glycine

HCID 71567D-Phenylalanine

HCID 444080N-Methyl-L-valine

HCID 70105704-tert-Butyl hydrogen L-aspartate

HCID 21863450Trifluoroacetic acid methylene chloride

HCID 178491778HCID 178491778, compound

HCID 178491779HCID 178491779, compound

Product 1

HCID 178491777HCID 178491777, compound

Procedure

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.

Sources & evidence

ORD record: ord-8a1f3e9205a64558bb261b5185b2c6ca
Source dataset: uspto-grants-2006_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07053041B1

Linked notes

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