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Clavanin-E

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Clavanin E has antimicrobial activity. The source of Clavanin E is invertebrate Styela clava.

Category

Functional Peptides

Catalog number

BAT-013431

Molecular Formula

C130H193N35O25

Molecular Weight

2646.14

Specification
Reference Reading

IUPAC Name

(2S)-2-[[2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S,3S)-2-[[(2S,3S)-2-[[(2S)-6-amino-2-[[2-[[(2S)-2-[[(2S)-2-[[(2S)-6-amino-2-[[(2S)-2-[[(2S)-2-amino-1-hydroxy-4-methylpentylidene]amino]-1-hydroxy-3-phenylpropylidene]amino]-1-hydroxyhexylidene]amino]-1-hydroxy-4-methylpentylidene]amino]-1-hydroxy-4-methylpentylidene]amino]-1-hydroxyethylidene]amino]-1-hydroxyhexylidene]amino]-1-hydroxy-3-methylpentylidene]amino]-1-hydroxy-3-methylpentylidene]amino]-1-hydroxy-3-(1H-imidazol-5-yl)propylidene]amino]-1-hydroxy-3-(1H-imidazol-5-yl)propylidene]amino]-1-hydroxy-3-methylbutylidene]amino]-1-hydroxyethylidene]amino]-N-[(2S)-1-[(2S)-1-[(2S)-1-[2-[(2S)-1-[(2S)-1,3-dihydroxy-1-[(2S)-1-hydroxy-1-[(2S)-1-hydroxy-1-[(2S)-1-hydroxy-1-imino-3-phenylpropan-2-yl]imino-3-methylbutan-2-yl]imino-3-(1H-imidazol-5-yl)propan-2-yl]iminopropan-2-yl]imino-1-hydroxy-3-phenylpropan-2-yl]imino-2-hydroxyethyl]imino-1-hydroxy-3-(1H-imidazol-5-yl)propan-2-yl]imino-1-hydroxy-3-methylbutan-2-yl]imino-1-hydroxy-3-phenylpropan-2-yl]butanediimidic acid

Purity

>97% by HPLC

Sequence

LFKLLGKIIHHVGNFVHGFSHVF

InChI

InChI=1S/C130H193N35O25/c1-17-77(15)109(165-130(190)110(78(16)18-2)164-116(176)88(43-31-33-45-131)147-103(168)63-140-113(173)91(48-72(5)6)153-117(177)92(49-73(7)8)154-115(175)89(44-32-34-46-132)150-119(179)94(52-81-39-27-21-28-40-81)152-112(172)87(133)47-71(3)4)129(189)159-97(55-84-60-137-68-144-84)120(180)156-98(56-85-61-138-69-145-85)123(183)161-106(74(9)10)126(186)142-65-105(170)149-100(58-102(134)167)121(181)155-95(53-82-41-29-22-30-42-82)122(182)162-108(76(13)14)128(188)158-96(54-83-59-136-67-143-83)114(174)141-64-104(169)148-93(51-80-37-25-20-26-38-80)118(178)160-101(66-166)125(185)157-99(57-86-62-139-70-146-86)124(184)163-107(75(11)12)127(187)151-90(111(135)171)50-79-35-23-19-24-36-79/h19-30,35-42,59-62,67-78,87-101,106-110,166H,17-18,31-34,43-58,63-66,131-133H2,1-16H3,(H2,134,167)(H2,135,171)(H,136,143)(H,137,144)(H,138,145)(H,139,146)(H,140,173)(H,141,174)(H,142,186)(H,147,168)(H,148,169)(H,149,170)(H,150,179)(H,151,187)(H,152,172)(H,153,177)(H,154,175)(H,155,181)(H,156,180)(H,157,185)(H,158,188)(H,159,189)(H,160,178)(H,161,183)(H,162,182)(H,163,184)(H,164,176)(H,165,190)/t77-,78-,87-,88-,89-,90-,91-,92-,93-,94-,95-,96-,97-,98-,99-,100-,101-,106-,107-,108-,109-,110-/m0/s1

InChI Key

YWTSDCFHLUVGBL-KPXZFSBNSA-N

Canonical SMILES

CCC(C)C(C(=NC(C(C)CC)C(=NC(CC1=CN=CN1)C(=NC(CC2=CN=CN2)C(=NC(C(C)C)C(=NCC(=NC(CC(=N)O)C(=NC(CC3=CC=CC=C3)C(=NC(C(C)C)C(=NC(CC4=CN=CN4)C(=NCC(=NC(CC5=CC=CC=C5)C(=NC(CO)C(=NC(CC6=CN=CN6)C(=NC(C(C)C)C(=NC(CC7=CC=CC=C7)C(=N)O)O)O)O)O)O)O)O)O)O)O)O)O)O)O)O)N=C(C(CCCCN)N=C(CN=C(C(CC(C)C)N=C(C(CC(C)C)N=C(C(CCCCN)N=C(C(CC8=CC=CC=C8)N=C(C(CC(C)C)N)O)O)O)O)O)O)O

1. Immunolocalization of clavanins in Styela clava hemocytes

Lorenzo P Menzel, In Hee Lee, Birgitta Sjostrand, Robert I Lehrer Dev Comp Immunol. 2002 Jul;26(6):505-15. doi: 10.1016/s0145-305x(02)00010-1.

Antimicrobial peptides play an important role in innate host defenses against infection. Clavanins are histidine-rich, amidated, 23-residue alpha-helical antimicrobial peptides that were isolated from a mixed population of Styela clava hemocytes. To learn which types of hemocytes contained clavanins, we raised a polyclonal antibody that recognized five different clavanins, and used it to localize these peptides by light and electron microscopy. Clavanins were present in the cytoplasmic granules and/or cytoplasm of five different types of granulocytes and they also occurred throughout the cytoplasm of macrophages. The orange G component of Mallory's trichrome stain had a high affinity for clavanins, and for the cytoplasmic granules of S. clava's hemocytes. Semiquantitative analysis of acid urea-PAGE gels suggested that clavanins and styelins comprised between 10 and 20% of the total cellular protein of eosinophilic granulocytes. Orange G and the century-old trichrome stain may provide simple screening tools for identifying cells that contain large amounts of antimicrobial peptides in mixed hemocyte populations.

3. Clavanins, alpha-helical antimicrobial peptides from tunicate hemocytes

I H Lee, C Zhao, Y Cho, S S Harwig, E L Cooper, R I Lehrer FEBS Lett. 1997 Jan 3;400(2):158-62. doi: 10.1016/s0014-5793(96)01374-9.

Hemocytes from the invertebrate Styela clava, a solitary tunicate, contained a family of four alpha-helical antimicrobial peptides that were purified, sequenced and named clavanins A, B, C and D. Each clavanin contained 23 amino acid residues and was C-terminally amidated. The tunicate peptides resembled magainins in size, primary sequence and antibacterial activity. Synthetic clavanin A was prepared and displayed comparable antimicrobial activity to magainins and cecropins. The presence of alpha-helical antimicrobial peptides in the hemocytes of a urochordate suggests that such peptides are primeval effectors of innate immunity in the vertebrate lineage.