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Fibrinopeptide information


Fibrinopeptide A
Names
IUPAC name
(4S)-4-[[2-[[(2S)-2-[[(2S)-2-[[(2S)-2-aminopropanoyl]amino]-3-carboxypropanoyl]amino]-3-hydroxypropanoyl]amino]acetyl]amino]-5-[[2-[[(2S)-3-carboxy-1-[[(2S)-1-[[1-[[(2S)-1-[[(2S)-4-carboxy-1-[[2-[[2-[[2-[[(2S)-1-[[(1S)-1-carboxy-4-(diaminomethylideneamino)butyl]amino]-3-methyl-1-oxobutan-2-yl]amino]-2-oxoethyl]amino]-2-oxoethyl]amino]-2-oxoethyl]amino]-1-oxobutan-2-yl]amino]-1-oxopropan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-1-oxo-3-phenylpropan-2-yl]amino]-1-oxopropan-2-yl]amino]-2-oxoethyl]amino]-5-oxopentanoic acid
Other names
Fibrinopeptide A; Fibrinopeptide A (human); FpA; FPA
Identifiers
CAS Number
  • 25422-31-5
3D model (JSmol)
  • Interactive image
ChemSpider
  • 17286499
PubChem CID
  • 25078015
InChI
  • InChI=1S/C63H97N19O26/c1-29(2)19-37(57(102)73-32(6)53(98)76-35(15-17-48(91)92)55(100)70-24-43(85)68-23-42(84)69-25-46(88)82-51(30(3)4)61(106)77-36(62(107)108)13-10-18-67-63(65)66)79-58(103)38(20-33-11-8-7-9-12-33)80-59(104)39(21-49(93)94)75-45(87)27-71-54(99)34(14-16-47(89)90)74-44(86)26-72-56(101)41(28-83)81-60(105)40(22-50(95)96)78-52(97)31(5)64/h7-9,11-12,29-32,34-41,51,83H,10,13-28,64H2,1-6H3,(H,68,85)(H,69,84)(H,70,100)(H,71,99)(H,72,101)(H,73,102)(H,74,86)(H,75,87)(H,76,98)(H,77,106)(H,78,97)(H,79,103)(H,80,104)(H,81,105)(H,82,88)(H,89,90)(H,91,92)(H,93,94)(H,95,96)(H,107,108)(H4,65,66,67)/t31-,32-,34-,35-,36-,37?,38-,39-,40-,41-,51-/m0/s1
    Key: JWICNZAGYSIBAR-LEEGLKINSA-N
SMILES
  • C[C@@H](C(=O)N[C@@H](CC(=O)O)C(=O)N[C@@H](CO)C(=O)NCC(=O)N[C@@H](CCC(=O)O)C(=O)NCC(=O)N[C@@H](CC(=O)O)C(=O)N[C@@H](CC1=CC=CC=C1)C(=O)NC(CC(C)C)C(=O)N[C@@H](C)C(=O)N[C@@H](CCC(=O)O)C(=O)NCC(=O)NCC(=O)NCC(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CCCN=C(N)N)C(=O)O)N
Properties
Chemical formula
 C63H97N19O26
Molar mass 1536.57 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references
Fibrinopeptide B
Names
IUPAC name
(4S)-4-[[(2S)-2-[[(2S)-4-amino-2-[[(2S)-2-[[(2S)-4-amino-2-[[(2S)-3-methyl-2-[[2-[[(2S)-5-oxopyrrolidine-2-carbonyl]amino]acetyl]amino]butanoyl]amino]-4-oxobutanoyl]amino]-3-carboxypropanoyl]amino]-4-oxobutanoyl]amino]-4-carboxybutanoyl]amino]-5-[[2-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(1S)-4-carbamimidamido-1-carboxybutyl]amino]-1-oxopropan-2-yl]amino]-3-hydroxy-1-oxopropan-2-yl]amino]-1-oxo-3-phenylpropan-2-yl]amino]-1-oxo-3-phenylpropan-2-yl]amino]-2-oxoethyl]amino]-5-oxopentanoic acid
Other names
Fibrinopeptide B; Fibrinopeptide B (human); FpB; FPB
Identifiers
CAS Number
  • 36204-23-6
3D model (JSmol)
  • Interactive image
ChemSpider
  • 17288791
PubChem CID
  • 16132131
InChI
  • InChI=1S/C66H93N19O25/c1-31(2)53(85-49(91)29-73-55(99)35-16-19-47(89)75-35)64(108)83-42(26-46(68)88)61(105)82-43(27-52(96)97)62(106)81-41(25-45(67)87)60(104)78-37(18-21-51(94)95)57(101)77-36(17-20-50(92)93)56(100)72-28-48(90)76-39(23-33-11-6-4-7-12-33)58(102)80-40(24-34-13-8-5-9-14-34)59(103)84-44(30-86)63(107)74-32(3)54(98)79-38(65(109)110)15-10-22-71-66(69)70/h4-9,11-14,31-32,35-44,53,86H,10,15-30H2,1-3H3,(H2,67,87)(H2,68,88)(H,72,100)(H,73,99)(H,74,107)(H,75,89)(H,76,90)(H,77,101)(H,78,104)(H,79,98)(H,80,102)(H,81,106)(H,82,105)(H,83,108)(H,84,103)(H,85,91)(H,92,93)(H,94,95)(H,96,97)(H,109,110)(H4,69,70,71)/t32-,35-,36-,37-,38-,39-,40-,41-,42-,43-,44-,53-/m0/s1
    Key: MYRIFIVQGRMHRF-OECXYHNASA-N
SMILES
  • C[C@@H](C(=O)N[C@@H](CCCNC(=N)N)C(=O)O)NC(=O)[C@H](CO)NC(=O)[C@H](CC1=CC=CC=C1)NC(=O)[C@H](CC2=CC=CC=C2)NC(=O)CNC(=O)[C@H](CCC(=O)O)NC(=O)[C@H](CCC(=O)O)NC(=O)[C@H](CC(=O)N)NC(=O)[C@H](CC(=O)O)NC(=O)[C@H](CC(=O)N)NC(=O)[C@H](C(C)C)NC(=O)CNC(=O)[C@@H]3CCC(=O)N3
Properties
Chemical formula
 C66H93N19O25
Molar mass 1552.569 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

The fibrinopeptides, fibrinopeptide A (FpA) and fibrinopeptide B (FpB), are peptides which are located in the central region of the fibrous glycoprotein fibrinogen (factor I) and are cleaved by the enzyme thrombin (factor IIa) to convert fibrinogen into covalently-linked fibrin (factor IA) monomers.[1][2] The N-terminal FpA is cleaved from the Aα chains of fibrinogen and FpB from the Bβ chains of fibrinogen, with FpA released before FpB.[3][4] Subsequent to their formation, fibrin monomers are converted to cross-linked fibrin polymers by the action of thrombin-activated factor XIII (fibrin stabilizing factor), and these fibrin polymers form the backbone of a thrombus (blood clot).[2] Hence, the fibrinopeptides are sensitive markers of fibrinogenesis (fibrin generation), thrombin activity, and coagulation.[5][6][7][8]

FpA is a 16-amino acid peptide.[8] The half-life of FpA is very short at approximately 3 to 5 minutes.[5][8] Hence, FpA levels provide a relatively transient measure of coagulation activation.[8]

Levels of FpA increase with age.[5] FpA levels also gradually increase throughout pregnancy.[9][10] Likewise, FpA levels have been reported to increase with estrogen therapy, including with combined birth control pills and menopausal hormone therapy, although research on FpA levels with these therapies appears to be relatively limited.[11][12][13][7]

  1. ^ Weisel JW (2005). "Fibrinogen and fibrin". Adv Protein Chem. Advances in Protein Chemistry. 70: 247–99. doi:10.1016/S0065-3233(05)70008-5. ISBN 9780120342709. PMID 15837518.
  2. ^ a b Gentry PA (November 2004). "Comparative aspects of blood coagulation". Vet J. 168 (3): 238–51. doi:10.1016/j.tvjl.2003.09.013. PMID 15501141.
  3. ^ Wolberg AS (September 2012). "Determinants of fibrin formation, structure, and function". Curr Opin Hematol. 19 (5): 349–56. doi:10.1097/MOH.0b013e32835673c2. PMID 22759629. S2CID 11358104.
  4. ^ O'Riordan MN, Higgins JR (June 2003). "Haemostasis in normal and abnormal pregnancy". Best Practice & Research Clinical Obstetrics & Gynaecology. 17 (3): 385–396. doi:10.1016/S1521-6934(03)00019-1. ISSN 1521-6934. PMID 12787533.
  5. ^ a b c Mannucci PM (October 1994). "Mechanisms, markers and management of coagulation activation". Br Med Bull. 50 (4): 851–70. doi:10.1093/oxfordjournals.bmb.a072930. PMID 7804735.
  6. ^ Vincent Marks, Thomas Cantor, Dusan Mesko, Rudolf Pullmann, Gabriela Nosalova (6 December 2012). Differential Diagnosis by Laboratory Medicine: A Quick Reference for Physicians. Springer Science & Business Media. pp. 443–. ISBN 978-3-642-55600-5. OCLC 1262382180.
  7. ^ a b Farris M, Bastianelli C, Rosato E, Brosens I, Benagiano G (October 2017). "Pharmacodynamics of combined estrogen-progestin oral contraceptives: 2. effects on hemostasis". Expert Rev Clin Pharmacol. 10 (10): 1129–1144. doi:10.1080/17512433.2017.1356718. PMID 28712325. S2CID 205931204.
  8. ^ a b c d Merlini PA, Ardissino D (1995). "Laboratory Measurement of Thrombin Activity--What Every Clinician Scientist Needs to Know". J Thromb Thrombolysis. 2 (2): 85–92. doi:10.1007/BF01064374. PMID 10608009. S2CID 28203940.
  9. ^ Hellgren M (April 2003). "Hemostasis during normal pregnancy and puerperium". Semin Thromb Hemost. 29 (2): 125–30. doi:10.1055/s-2003-38897. PMID 12709915. S2CID 22082884.
  10. ^ Koltsova E, Balandina A, Serebriyskiy I, Vuimo T, Panteleev M, Ataullakhanov F (21 September 2016). "Classic and Global Hemostasis Testing in Pregnancy and during Pregnancy Complications". Seminars in Thrombosis and Hemostasis. 42 (7): 696–716. doi:10.1055/s-0036-1592303. eISSN 1098-9064. ISSN 0094-6176. PMID 27652600. S2CID 19571354.
  11. ^ Douxfils J, Morimont L, Bouvy C (November 2020). "Oral Contraceptives and Venous Thromboembolism: Focus on Testing that May Enable Prediction and Assessment of the Risk". Semin Thromb Hemost. 46 (8): 872–886. doi:10.1055/s-0040-1714140. PMID 33080636. S2CID 224821517.
  12. ^ Canonico M (July 2014). "Hormone therapy and hemostasis among postmenopausal women: a review" (PDF). Menopause. 21 (7): 753–62. doi:10.1097/GME.0000000000000296. PMID 24937030. S2CID 20851353.
  13. ^ Baker L, Meldrum KK, Wang M, Sankula R, Vanam R, Raiesdana A, Tsai B, Hile K, Brown JW, Meldrum DR (December 2003). "The role of estrogen in cardiovascular disease". J Surg Res. 115 (2): 325–44. doi:10.1016/s0022-4804(03)00215-4. PMID 14697301.

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samples. Reptilase also differs from thrombin by releasing fibrinopeptide A, but not fibrinopeptide B, in its cleavage of fibrinogen.[citation needed] Van...

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Fibrinogen

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fibrinogen to form individual fibrin strands plus two small polypeptides, fibrinopeptides A and B derived from these respective chains. The individual fibrin...

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Fibrin

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and galactose linkage. Fibrin is formed after thrombin cleavage of fibrinopeptide A (FPA) from fibrinogen Aalpha-chains, thus initiating fibrin polymerization...

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Tyrosine sulfation

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be sulfated. Sulfation was first discovered by Bettelheim in bovine fibrinopeptide B in 1954 and later found to be present in animals and plants but not...

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Dysfibrinogenemia

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by thrombin to form individual fibrin strands plus the respective fibrinopeptides A and B formed from this cleavage. In the final common pathway fibrin...

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Thrombin

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conversion of fibrinogen into fibrin, thrombin catalyzes the cleavage of fibrinopeptides A and B from the respective Aα and Bβ chains of fibrinogen to form...

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FPA

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in the United States Food Products Association, in the United States Fibrinopeptide A, a compound in coagulation Floating Point Accelerator, a math coprocessor...

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Evidence of common descent

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for rRNA, which is highly conserved, and DNA sequences coding for fibrinopeptides, amino acid chains discarded during the formation of fibrin, which...

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FPB

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of Trade Unions of Belarus Femoropopliteal bypass, a type of surgery Fibrinopeptide B, a compound in coagulation Film and Publication Board, in South Africa...

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Subarachnoid hemorrhage

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known as (Virchow-Robin spaces). The released clotting factors like; fibrinopeptides, thromboxane A2 and others lead to microthrombosis around near vessels...

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prothrombin fragment 1+2 (F1+2), thrombin–antithrombin complex (TAT), fibrinopeptide A (FpA), fibrin monomers (FMs), plasmin-α2-antiplasmin complex (PAP)...

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Neutral theory of molecular evolution

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extremely high evolutionary rates were observed in proteins such as fibrinopeptides and the C chain of the proinsulin molecule, which both have little...

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Venombin A

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Selective cleavage of Arg- bond in fibrinogen, to form fibrin, and release fibrinopeptide A. The specificity of further degradation of fibrinogen varies with...

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C5orf24

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PMID 21802404. O'Neil PB, Doolittle RF (1973). "Mammalian Phylogeny Based on Fibrinopeptide Amino Acid Sequences". Systematic Zoology. 22 (4): 590–595. doi:10.2307/2412963...

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Outline of immunology

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activation markers Prothrombin fragments 1+2 Thrombin–antithrombin complex Fibrinopeptide A Fibrin monomers Activated protein C–protein C inhibitor Fibrinolysis...

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Cerastocytin

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thrombin at 1nM. Cerastocytin contains a hydrophobic domain that binds fibrinopeptide A and in the 3-D confirmation looks very similar to the analogous region...

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Chromosome 9 open reading frame 43

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diverge more quickly than cytochrome c but slower than fast evolving fibrinopeptides. A table of orthologous proteins constructed using BLAST contains a...

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Batroxobin

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y’-chain (yA,y’) When fibrinogen is cleaved by thrombin, it releases fibrinopeptide A or B. Thrombin acts on two exosites to fibrinogen. Exosite 1 mediates...

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C16orf90

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mutation rate as seen in the graph to the right comparing C16orf90 with fibrinopeptides, hemoglobin, and cytochrome C. The orthologs are sorted by increasing...

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Biomarkers of multiple sclerosis

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patients compared to PrMS (p<0.05), whereas the signals of Fibrinogen and Fibrinopeptide A were significantly downregulated in CIS compared to PrMS patients...

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Venombin AB

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Selective cleavage at Arg- bonds in fibrinogen to form fibrin and release fibrinopeptides A and B This enzyme is isolated from the venom of the Gaboon viper...

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C1orf94

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protein. C1orf94 evolved faster than both Cytochrome C and less than fibrinopeptides. C1orf94 has no paralogs. Orthologs were identified using NCBI BLASTp...

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LSMEM1

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Lysine carboxypeptidase

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cleavage of C-terminal arginine. Other lesser studied substrates include fibrinopeptides which are involved in blood clotting. This enzyme is extremely important...

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