Fmoc-Gly-OH → L-Phenylalanine

HRID 1441192

Reaktionsgleichung

Reaktionsgleichung von HRID 1441192
[C:1]([N:18](C)[C@H:19]([C:27]([OH:29])=[O:28])[CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)(OCC1C2C(=CC=CC=2)C2C1=CC=CC=2)=O.N(C(OCC1C2C(=CC=CC=2)C2C1=CC=CC=2)=O)[C@@H](C(O)=O)CC(=O)OC(C)(C)C.[NH:61](C(OCC1C2C(=CC=CC=2)C2C1=CC=CC=2)=O)[C@H:62]([C:70]([OH:72])=[O:71])[CH2:63][C:64]1[CH:69]=[CH:68][CH:67]=[CH:66][CH:65]=1.[NH:90](C(OCC1C2C(=CC=CC=2)C2C1=CC=CC=2)=O)[C@H:91]([C:102]([OH:104])=[O:103])[CH2:92][C:93]1[C:101]2[C:96](=[CH:97][CH:98]=[CH:99][CH:100]=2)[NH:95][CH:94]=1.N(C(OCC1C2C(=CC=CC=2)C2C1=CC=CC=2)=O)CC(O)=O.N(C(OCC1C2C(=CC=CC=2)C2C1=CC=CC=2)=O)[C@H](C(O)=O)CCCC>>[NH:18]([CH3:1])[C@H:19]([C:27]([OH:29])=[O:28])[CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.[NH2:61][C@H:62]([C:70]([OH:72])=[O:71])[CH2:63][C:64]1[CH:69]=[CH:68][CH:67]=[CH:66][CH:65]=1.[NH2:90][C@H:91]([C:102]([OH:104])=[O:103])[CH2:92][C:93]1[C:101]2[C:96](=[CH:97][CH:98]=[CH:99][CH:100]=2)[NH:95][CH:94]=1

Komponenten

9

Edukt 6

HCID 93124Fmoc-Gly-OHHCID 978331Fmoc-phenylalanineHCID 978343Fmoc-L-tryptophanHCID 978356(S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)(methyl)amino)-3-phenylpropanoic acidHCID 7009636(2S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)hexanoic acidHCID 70188164-tert-Butyl N-((9H-Fluoren-9-ylmethoxy)carbonyl)-D-aspartate

Produkt 3

HCID 6140L-PhenylalanineHCID 6305L-TryptophanHCID 6951135N-Methylphenylalanine

Versuchsvorschrift

By following essentially the procedure of Table 2 and sequentially coupling Fmoc-MePhe-OH, Fmoc-DAsp(OtBu)-OH, Fmoc-Phe-OH, Fmoc-Trp-OH, Fmoc-Gly-OH, Fmoc-Ahx-OH and Hpa-OSu, the title compound was prepared. Amino Acid analysis following acid decomposition gave Asp 1.01 (1), Gly 0.99 (1), MePhe 1.06 (1), Ahx 1.02 (1), Trp 1.06 (1), Phe 0.94 (1), NH3 0.82. MS (FAB): m/e 931 (M-H)-.

Quellen und Nachweise

ORD-Eintrag
ord-cb08aa5f47424d19ac33ed09291c68ca
Quelldatensatz
uspto-grants-1996_03
Patentnummer
US05502164

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