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Hirullin

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Hirullin is originally isolated from the leech Hirudinaria manillensis. It is a hirudin-based fibrinogen recognition peptide inhibitor, which binds efficiently to thrombin (IC50= 4.2 µM, in bovine).

Category

Peptide Inhibitors

Catalog number

BAT-015928

CAS number

131147-81-4

Molecular Formula

C68H96N14O29

Molecular Weight

1573.57

Specification
Reference Reading

IUPAC Name

(2S)-5-amino-2-[[(2S)-2-[[(2S,3S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-amino-3-hydroxypropanoyl]amino]-3-carboxypropanoyl]amino]-3-phenylpropanoyl]amino]-4-carboxybutanoyl]amino]-4-carboxybutanoyl]amino]-3-phenylpropanoyl]amino]-3-hydroxypropanoyl]amino]-4-methylpentanoyl]amino]-3-carboxypropanoyl]amino]-3-carboxypropanoyl]amino]-3-methylpentanoyl]amino]-4-carboxybutanoyl]amino]-5-oxopentanoic acid

Synonyms

H-SER-ASP-PHE-GLU-GLU-PHE-SER-LEU-ASP-ASP-ILE-GLU-GLN-OH

Purity

95%

Sequence

SDFEEFSLDDIEQ

Storage

Store at -20°C

InChI

InChI=1S/C68H96N14O29/c1-5-33(4)55(67(109)73-39(19-23-51(90)91)58(100)74-40(68(110)111)16-20-48(70)85)82-65(107)46(29-54(96)97)80-64(106)45(28-53(94)95)79-60(102)41(24-32(2)3)76-66(108)47(31-84)81-62(104)43(26-35-14-10-7-11-15-35)77-59(101)38(18-22-50(88)89)71-57(99)37(17-21-49(86)87)72-61(103)42(25-34-12-8-6-9-13-34)78-63(105)44(27-52(92)93)75-56(98)36(69)30-83/h6-15,32-33,36-47,55,83-84H,5,16-31,69H2,1-4H3,(H2,70,85)(H,71,99)(H,72,103)(H,73,109)(H,74,100)(H,75,98)(H,76,108)(H,77,101)(H,78,105)(H,79,102)(H,80,106)(H,81,104)(H,82,107)(H,86,87)(H,88,89)(H,90,91)(H,92,93)(H,94,95)(H,96,97)(H,110,111)/t33-,36-,37-,38-,39-,40-,41-,42-,43-,44-,45-,46-,47-,55-/m0/s1

InChI Key

WUDUBJRKXIMUCO-DUBUDNBPSA-N

Canonical SMILES

CCC(C)C(C(=O)NC(CCC(=O)O)C(=O)NC(CCC(=O)N)C(=O)O)NC(=O)C(CC(=O)O)NC(=O)C(CC(=O)O)NC(=O)C(CC(C)C)NC(=O)C(CO)NC(=O)C(CC1=CC=CC=C1)NC(=O)C(CCC(=O)O)NC(=O)C(CCC(=O)O)NC(=O)C(CC2=CC=CC=C2)NC(=O)C(CC(=O)O)NC(=O)C(CO)N

1.The C-terminal binding domain of hirullin P18. Antithrombin activity and comparison to hirudin peptides.

Krstenansky JL1, Owen TJ, Yates MT, Mao SJ. FEBS Lett. 1990 Sep 3;269(2):425-9.

Hirullin P18 is a 61-amino acid hirudin-related protein having potent antithrombin activity. Similar to hirudin, it contains a highly acidic C-terminus, but has a significantly different sequence from any other known hirudin variant. The present study demonstrates that the C-terminal fragment acetyl-hirullin P18(41-62) [corrected] possesses an antithrombin potency similar to that of acetyl-desulfatohirudin(45-65). Additionally, like the hirudin fragment analog, it inhibits fibrin-clot formation by binding to a non-catalytic site on thrombin. Sequential shortening of the hirullin P18 C-terminal fragment demonstrates the critical nature of Phe51, which corresponds to the important Phe56 residue of hirudin. Although the sequences of hirullin P18(54-61) and hirudin(59-65) have substantial differences, the C-terminal functional domain represented by hirullin P18(50-61) appears to be comparable to hirudin(55-65) in terms of its functional role in antithrombin activity.