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MF: C59H89N19O13S
Appearance: White solid
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Definition |
ChEBI: A ten-membered synthetic oligopeptide consisting of D-Arg, Arg, Pro, Hyp, Gly, Thi, Ser, D-Tic, Oic, and Arg residues joined in sequrence. A bradykinin receptor antagonist used as its acetate salt for the treatment of acut attacks of hereditary angioedema in adult patients. |
InChI:InChI=1/C59H89N19O13S/c60-37(14-5-19-67-57(61)62)48(82)72-38(15-6-20-68-58(63)64)52(86)75-22-8-18-43(75)54(88)77-30-35(80)26-44(77)50(84)70-28-47(81)71-40(27-36-13-9-23-92-36)49(83)74-41(31-79)53(87)76-29-34-12-2-1-10-32(34)24-46(76)55(89)78-42-17-4-3-11-33(42)25-45(78)51(85)73-39(56(90)91)16-7-21-69-59(65)66/h1-2,9-10,12-13,23,33,35,37-46,79-80H,3-8,11,14-22,24-31,60H2,(H,70,84)(H,71,81)(H,72,82)(H,73,85)(H,74,83)(H,90,91)(H4,61,62,67)(H4,63,64,68)(H4,65,66,69)/t33-,35+,37+,38?,39-,40-,41-,42-,43?,44?,45?,46?/m0/s1
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Fmoc-(D)Arg(Pbf)-Arg(Pbf)-Pro-Hyr(tBu)-Gly-OH
Fmoc-Ser(tBu)-OH
N-Fmoc-D-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid
1‐fluorenylmethoxycarbonyl-(2S,3aS,7aS)‐octahydroindole‐2‐carboxylic acid
Fmoc-β-(2-thienyl)-L-alanine
Nα-(9-fluorenylmethyloxycarbonyl)-Nγ-2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl-L-arginine
D-Arg-Arg-Pro-Hyp-Gly-Thi-Ser-D-Tic-Oic-Arg
| Conditions | Yield |
|---|---|
|
Nα-(9-fluorenylmethyloxycarbonyl)-Nγ-2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl-L-arginine;
With
dmap; acetic anhydride; N-ethyl-N,N-diisopropylamine; diisopropyl-carbodiimide;
In
N,N-dimethyl-formamide;
at 20 ℃;
for 0.5h;
With
piperidine;
In
N,N-dimethyl-formamide;
at 20 ℃;
Fmoc-(D)Arg(Pbf)-Arg(Pbf)-Pro-Hyr(tBu)-Gly-OH; Fmoc-Ser(tBu)-OH; N-Fmoc-D-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid; 1‐fluorenylmethoxycarbonyl-(2S,3aS,7aS)‐octahydroindole‐2‐carboxylic acid; Fmoc-β-(2-thienyl)-L-alanine;
Further stages;
|
70% |
N-(fluoren-9-ylmethoxycarbonyl)glycine
Fmoc-Pro-OH
Fmoc-Ser(tBu)-OH
(2S,4R)-4-tert-butoxy-1-(9H-fluoren-9-ylmethoxycarbonyl)pyrrolidine-2-carboxylic acid
N-Fmoc-D-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid
1‐fluorenylmethoxycarbonyl-(2S,3aS,7aS)‐octahydroindole‐2‐carboxylic acid
Fmoc-β-(2-thienyl)-L-alanine
Nα-(9-fluorenylmethyloxycarbonyl)-Nγ-2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl-L-arginine
N-α-[(9H-fluoren-9-ylmethoxy)carbonyl]-NG-(2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl)-D-arginine
D-Arg-Arg-Pro-Hyp-Gly-Thi-Ser-D-Tic-Oic-Arg
| Conditions | Yield |
|---|---|
|
Nα-(9-fluorenylmethyloxycarbonyl)-Nγ-2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl-L-arginine;
With
N-ethyl-N,N-diisopropylamine;
In
N,N-dimethyl-formamide;
at 20 ℃;
With
methanol; N-ethyl-N,N-diisopropylamine;
In
N,N-dimethyl-formamide;
N-(fluoren-9-ylmethoxycarbonyl)glycine; Fmoc-Pro-OH; Fmoc-Ser(tBu)-OH; (2S,4R)-4-tert-butoxy-1-(9H-fluoren-9-ylmethoxycarbonyl)pyrrolidine-2-carboxylic acid; N-Fmoc-D-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid; 1‐fluorenylmethoxycarbonyl-(2S,3aS,7aS)‐octahydroindole‐2‐carboxylic acid; Fmoc-β-(2-thienyl)-L-alanine; N-α-[(9H-fluoren-9-ylmethoxy)carbonyl]-NG-(2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl)-D-arginine;
Reagent/catalyst;
Temperature;
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N-(fluoren-9-ylmethoxycarbonyl)glycine
Fmoc-Pro-OH
Fmoc-Ser(tBu)-OH
(2S,4R)-4-tert-butoxy-1-(9H-fluoren-9-ylmethoxycarbonyl)pyrrolidine-2-carboxylic acid