A citrullinated form of LL-37
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Citrullinated LL-37 Peptide (trifluoroacetate salt)

Item No. 30987

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Synonyms
  • Citrullinated Antibacterial Peptide LL-37
Molecular Formula
C205H335N55O58 • XCF3COOH
Formula Weight
4498.3
MW
4,497.2
Formulation (Request formulation change)
1 mg of lyophilized peptide
SMILES
[H]N[C@H](C(N[C@H](C(NCC(N[C@@H](CC(O)=O)C(N[C@@H](CC1=CC=CC=C1)C(N[C@@H](CC2=CC=CC=C2)C(N[C@H](C(N[C@H](C(N[C@H](C(N[C@H](C(N[C@H](C(N[C@H](C(N[C@]([H])(C(NCC(N[C@H](C(N[C@H](C(N[C@@H](CC3=CC=CC=C3)C(N[C@H](C(N[C@H](C(N[C@]([H])(C(N[C@H](C(N[C@H](C(N[C@H](C(N[C@]([H])(C(N[C@H](C(N[C@@H](CC(O)=O)C(N[C@@H](CC4=CC=CC=C4)C(N[C@H](C(N[C@H](C(N[C@H](C(N[C@H](C(N[C@H](C(N5CCC[C@H]5C(N[C@H](C(N[C@]([H])(C(N[C@H](C(N[C@H](C(O)=O)CO)=O)CCC(O)=O)=O)[C@H](O)C)=O)CCCNC(N)=O)=O)=O)C(C)C)=O)CC(C)C)=O)CC(N)=O)=O)CCCNC(N)=O)=O)CC(C)C)=O)=O)=O)CCCCN)=O)[C@@H](C)CC)=O)CCCNC(N)=O)=O)CCC(N)=O)=O)C(C)C)=O)[C@@H](C)CC)=O)CCCNC(N)=O)=O)CCCCN)=O)=O)CCC(O)=O)=O)CCCCN)=O)=O)[C@@H](C)CC)=O)CCCCN)=O)CCC(O)=O)=O)CCCCN)=O)CO)=O)CCCCN)=O)CCCNC(N)=O)=O)=O)=O)=O)=O)CC(C)C)=O)CC(C)C.FC(C(O)=O)(F)F
InChi Code
InChI=1S/C205H335N55O58.C2HF3O2/c1-20-114(16)162(256-179(291)128(66-40-46-86-211)230-176(288)135(74-78-155(268)269)238-170(282)125(63-37-43-83-208)236-192(304)148(106-261)252-174(286)126(64-38-44-84-209)229-171(283)129(67-47-87-220-201(215)314)235-185(297)142(98-119-55-29-24-30-56-119)247-187(299)144(100-121-59-33-26-34-60-121)248-189(301)146(102-158(274)275)228-154(267)104-225-167(279)138(94-109(6)7)243-166(278)122(212)93-108(4)5)194(306)226-105-153(266)227-123(61-35-41-81-206)168(280)237-136(75-79-156(270)271)177(289)246-141(97-118-53-27-23-28-54-118)184(296)233-124(62-36-42-82-207)169(281)231-131(69-49-89-222-203(217)316)181(293)258-164(116(18)22-3)197(309)254-160(112(12)13)195(307)241-134(73-77-151(213)264)175(287)232-132(70-50-90-223-204(218)317)180(292)257-163(115(17)21-2)196(308)240-127(65-39-45-85-210)172(284)251-147(103-159(276)277)190(302)249-143(99-120-57-31-25-32-58-120)186(298)244-139(95-110(8)9)183(295)234-130(68-48-88-221-202(216)315)173(285)250-145(101-152(214)265)188(300)245-140(96-111(10)11)191(303)255-161(113(14)15)199(311)260-92-52-72-150(260)193(305)239-133(71-51-91-224-205(219)318)182(294)259-165(117(19)263)198(310)242-137(76-80-157(272)273)178(290)253-149(107-262)200(312)313;3-2(4,5)1(6)7/h23-34,53-60,108-117,122-150,160-165,261-263H,20-22,35-52,61-107,206-212H2,1-19H3,(H2,213,264)(H2,214,265)(H,225,279)(H,226,306)(H,227,266)(H,228,267)(H,229,283)(H,230,288)(H,231,281)(H,232,287)(H,233,296)(H,234,295)(H,235,297)(H,236,304)(H,237,280)(H,238,282)(H,239,305)(H,240,308)(H,241,307)(H,242,310)(H,243,278)(H,244,298)(H,245,300)(H,246,289)(H,247,299)(H,248,301)(H,249,302)(H,250,285)(H,251,284)(H,252,286)(H,253,290)(H,254,309)(H,255,303)(H,256,291)(H,257,292)(H,258,293)(H,259,294)(H,268,269)(H,270,271)(H,272,273)(H,274,275)(H,276,277)(H,312,313)(H3,215,220,314)(H3,216,221,315)(H3,217,222,316)(H3,218,223,317)(H3,219,224,318);(H,6,7)/t114-,115-,116-,117+,122-,123-,124-,125-,126-,127-,128-,129-,130-,131-,132-,133-,134-,135-,136-,137-,138-,139-,140-,141-,14
InChi Key
IRXDEGNAJWHSLQ-YLLLKHBJSA-N
UniProt Accession №
P49913
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    1 mg

    $267

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    Product Description

    LL-37 is a cationic α-helical peptide expressed in human bone marrow, testis, granulocytes, and gingival epithelium and a variety of immune cells.1 It has antimicrobial and antiviral activity, and protein levels of LL-37 are increased in epithelial cells, macrophages, and neutrophils following bacterial infection in vitro.1,2,3,4 LL-37 can be citrullinated by protein arginine deiminase 2 (PAD2) and PAD4, a modification that reduces its antibacterial and antiviral activities.5 Citrullinated, unlike native, LL-37 does not prevent mortality in a mouse model of D-galactosamine-sensitized endotoxic shock.6 Citrullinated LL-37 has been found in neutrophil extracellular traps (NETs), as well as the serum of patients with rheumatoid arthritis (RA) and individuals without RA.7

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Weinberg, A., Krisanaprakornkit, S., and Dale, B.A. Epithelial antimicrobial peptides: Review and significance for oral applications. Crit. Rev. Oral Biol. Med. 9(4), 399-414 (1998).

    2. Rivas-Santiago, B., Hernandez-Pando, R., Carranza, C., et al. Expression of cathelicidin LL-37 during Mycobacterium tuberculosis infection in human alveolar macrophages, monocytes, neutrophils, and epithelial cells. Infect. Immun. 76(3), 935-941 (2008).

    3. Gudmundsson, G.H., Agerberth, B., Odeberg, J., et al. The human gene FALL39 and processing of the cathelin precursor to the antibacterial peptide LL-37 in granulocytes. Eur. J. Biochem. 238(2), 325-332 (1996).

    4. Ishiyama, M., Shiga, M., Sasamoto, K., et al. A new sulfonated tetrazolium salt that produces a highly water-soluble formazan dye. Chem. Pharm. Bull. 41(6), 1118-1122 (1993).

    5. Casanova, V., Sousa, F.H., Shakamuri, P., et al. Citrullination alters the antiviral and immunomodulatory activities of the human cathelicidin LL-37 during rhinovirus infection. Front. Immunol. 11, 85 (2020).

    6. Koziel, J., Bryzek, D., Sroka, A., et al. Citrullination alters immunomodulatory function of LL-37 essential for prevention of endotoxin-induced spesis. J. Immunol. 192(11), 5363-5372 (2014).

    7. Wong, A., Bryzek, D., Dobosz, E., et al. A novel biological role for peptidyl-arginine deiminases: Citrullination of cathelicidin LL-37 controls the immunostimulatory potential of cell-free DNA. J. Immunol. 200(7), 2327-2340 (2018).