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Antifreeze Polypeptide 6 (winter flounder)

* Please kindly note that our products are not to be used for therapeutic purposes and cannot be sold to patients.

Antifreeze polypeptides (AFP) have the common ability to lower the freezing point of serum, thus allowing fish to survive in sub-zero ocean temperatures. Type I AFPs are found in the blood of winter flounder, yellowtail flounder, Alaskan plaice, and the shorthorn and grubby sculpin. AFP37 (HPLC6) is isolated from the winter flounder, Pseudopleuronectes americanus, and consists of 37 amino acids arranged in three 11-residue repeats to form α-helices.

Category

Peptide Inhibitors

Catalog number

BAT-014689

CAS number

122604-16-4

Molecular Formula

C133H225N43O51

Molecular Weight

3242.47

Specification
Reference Reading

IUPAC Name

(4S)-4-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-6-amino-2-[[(2S)-2-[[(2S)-4-amino-2-[[(2S)-2-[[(2S)-2-[[(2S,3R)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S,3R)-2-[[(2S)-2-amino-3-carboxypropanoyl]amino]-3-hydroxybutanoyl]amino]propanoyl]amino]-3-hydroxypropanoyl]amino]-3-carboxypropanoyl]amino]propanoyl]amino]propanoyl]amino]propanoyl]amino]propanoyl]amino]propanoyl]amino]propanoyl]amino]-4-methylpentanoyl]amino]-3-hydroxybutanoyl]amino]propanoyl]amino]propanoyl]amino]-4-oxobutanoyl]amino]propanoyl]amino]hexanoyl]amino]propanoyl]amino]propanoyl]amino]propanoyl]amino]-5-[[(2S)-1-[[(2S,3R)-1-[[(2S)-1-[[(2S)-1-[[(2S)-4-amino-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S,3R)-1-[[(2S)-1-[[(1S)-4-carbamimidamido-1-carboxybutyl]amino]-1-oxopropan-2-yl]amino]-3-hydroxy-1-oxobutan-2-yl]amino]-1-oxopropan-2-yl]amino]-1-oxopropan-2-yl]amino]-1-oxopropan-2-yl]amino]-1-oxopropan-2-yl]amino]-1-oxopropan-2-yl]amino]-1-oxopropan-2-yl]amino]-1-oxopropan-2-yl]amino]-1,4-dioxobutan-2-yl]amino]-1-oxopropan-2-yl]amino]-1-oxopropan-2-yl]amino]-3-hydroxy-1-oxobutan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-5-oxopentanoic acid

Synonyms

AFP 6 (winter flounder); H-Asp-Thr-Ala-Ser-Asp-Ala-Ala-Ala-Ala-Ala-Ala-Leu-Thr-Ala-Ala-Asn-Ala-Lys-Ala-Ala-Ala-Glu-Leu-Thr-Ala-Ala-Asn-Ala-Ala-Ala-Ala-Ala-Ala-Ala-Thr-Ala-Arg-OH; L-alpha-aspartyl-L-threonyl-L-alanyl-L-seryl-L-alpha-aspartyl-L-alanyl-L-alanyl-L-alanyl-L-alanyl-L-alanyl-L-alanyl-L-leucyl-L-threonyl-L-alanyl-L-alanyl-L-asparagyl-L-alanyl-L-lysyl-L-alanyl-L-alanyl-L-alanyl-L-alpha-glutamyl-L-leucyl-L-threonyl-L-alanyl-L-alanyl-L-asparagyl-L-alanyl-L-alanyl-L-alanyl-L-alanyl-L-alanyl-L-alanyl-L-alanyl-L-threonyl-L-alanyl-L-arginine; HPLC-6 (winter flounder); AFP37 (winter flounder)

Appearance

White Lyophilized Powder

Purity

≥95%

Density

1.5±0.1 g/cm3

Sequence

DTASDAAAAAALTAANAKAAAELTAANAAAAAAATAR

Storage

Store at -20°C

Solubility

Soluble in Water

InChI

InChI=1S/C133H225N43O51/c1-48(2)41-81(167-114(208)66(21)152-104(198)57(12)146-99(193)53(8)142-98(192)52(7)145-102(196)56(11)150-108(202)62(17)158-124(218)85(46-91(188)189)171-127(221)86(47-177)172-117(211)71(26)163-129(223)93(74(29)179)174-119(213)77(135)43-90(186)187)125(219)175-94(75(30)180)130(224)160-63(18)109(203)154-68(23)116(210)169-84(45-88(137)183)123(217)159-69(24)112(206)164-78(35-32-33-39-134)120(214)156-60(15)106(200)148-58(13)103(197)151-65(20)111(205)165-79(37-38-89(184)185)121(215)170-82(42-49(3)4)126(220)176-95(76(31)181)131(225)161-64(19)110(204)153-67(22)115(209)168-83(44-87(136)182)122(216)157-61(16)107(201)149-55(10)101(195)144-51(6)97(191)141-50(5)96(190)143-54(9)100(194)147-59(14)105(199)155-72(27)118(212)173-92(73(28)178)128(222)162-70(25)113(207)166-80(132(226)227)36-34-40-140-133(138)139/h48-86,92-95,177-181H,32-47,134-135H2,1-31H3,(H2,136,182)(H2,137,183)(H,141,191)(H,142,192)(H,143,190)(H,144,195)(H,145,196)(H,146,193)(H,147,194)(H,148,200)(H,149,201)(H,150,202)(H,151,197)(H,152,198)(H,153,204)(H,154,203)(H,155,199)(H,156,214)(H,157,216)(H,158,218)(H,159,217)(H,160,224)(H,161,225)(H,162,222)(H,163,223)(H,164,206)(H,165,205)(H,166,207)(H,167,208)(H,168,209)(H,169,210)(H,170,215)(H,171,221)(H,172,211)(H,173,212)(H,174,213)(H,175,219)(H,176,220)(H,184,185)(H,186,187)(H,188,189)(H,226,227)(H4,138,139,140)/t50-,51-,52-,53-,54-,55-,56-,57-,58-,59-,60-,61-,62-,63-,64-,65-,66-,67-,68-,69-,70-,71-,72-,73+,74+,75+,76+,77-,78-,79-,80-,81-,82-,83-,84-,85-,86-,92-,93-,94-,95-/m0/s1

InChI Key

DOTNBIUQTZIHJP-CISJBLJSSA-N

Canonical SMILES

CC(C)CC(C(=O)NC(C(C)O)C(=O)NC(C)C(=O)NC(C)C(=O)NC(CC(=O)N)C(=O)NC(C)C(=O)NC(CCCCN)C(=O)NC(C)C(=O)NC(C)C(=O)NC(C)C(=O)NC(CCC(=O)O)C(=O)NC(CC(C)C)C(=O)NC(C(C)O)C(=O)NC(C)C(=O)NC(C)C(=O)NC(CC(=O)N)C(=O)NC(C)C(=O)NC(C)C(=O)NC(C)C(=O)NC(C)C(=O)NC(C)C(=O)NC(C)C(=O)NC(C)C(=O)NC(C(C)O)C(=O)NC(C)C(=O)NC(CCCNC(=N)N)C(=O)O)NC(=O)C(C)NC(=O)C(C)NC(=O)C(C)NC(=O)C(C)NC(=O)C(C)NC(=O)C(C)NC(=O)C(CC(=O)O)NC(=O)C(CO)NC(=O)C(C)NC(=O)C(C(C)O)NC(=O)C(CC(=O)O)N

1. Purification and characterization of winter flounder antifreeze peptide messenger ribonucleic acid

Y Lin, D J Long Biochemistry. 1980 Mar 18;19(6):1111-6. doi: 10.1021/bi00547a011.

The serum of winter flounder contains a group of small antifreeze peptides which lower the freezing point of their body fluids during the winter months. The poly(A)-containing mRNA coding for these peptides has been isolated from livers of the winter specimens. When the isolated antifreeze mRNA was analyzed by a denaturing polyacrylamide gel electrophoresis, at least two distinct bands approximately 450 nucleotides in length are visible. In a wheat germ cell-free protein synthetic system these mRNAs direct the synthesis of small peptides which can be precipitated by antisera against purified winter flounder antifreeze peptides. Full-length cDNA was synthesized from the isolated antifreeze mRNA by avian myeloblastosis reverse transcriptase. From the RNA excess hybridization kinetic analysis, there are probably three different mRNAs coding for the antifreeze peptides. Using the radioactive cDNA probe, it was estimated that 1% of the total RNA in liver of a January specimen is antifreeze mRNA. RNA from a summar specimen showed no significant hybridization even at high concentrations of RNA. These results indicate that the control of antifreeze peptide biosynthesis relies at least in part on the synthesis or degradation of translatable mRNA.

2. Single crystals of a winter flounder antifreeze polypeptide

D S Yang, Y J Chung, P Chen, J P Rose, C L Hew J Mol Biol. 1986 Jun 20;189(4):725. doi: 10.1016/0022-2836(86)90504-8.

Component 6 of the winter flounder's antifreeze polypeptides has been crystallized. The space group is P21, with cell parameters of a = 38.14 A, b = 37.19 A, c = 21.82 A, beta = 101.5 degrees. There are two molecules of 3300 Mr per asymmetric unit.

3. Molecular dynamics simulations of a winter flounder "antifreeze" polypeptide in aqueous solution

S M McDonald, J W Brady, P Clancy Biopolymers. 1993 Oct;33(10):1481-503. doi: 10.1002/bip.360331002.

A winter flounder antifreeze polypeptide (HPLC-6) has been studied in vacuo and in aqueous solution using molecular dynamics computer simulation techniques. The helical conformation of this polypeptide was found to be stable both in vacuum and in solution. The major stabilizing interactions were found to be the main-chain hydrogen bonds, a salt-bridge interaction, and solute-solvent hydrogen bonds. A significant bending in the middle of the polypeptide chain was observed both in vacuo and in solvent at 300 K. Possible causes of the bending are discussed. From simulations of mutant polypeptide molecules in vacuo, it is concluded that the bend in the native polypeptide was caused by side chain to backbone hydrogen bond competition involving the Thr 24 side chain and facilitated by strains on the helix resulting from the Lys 18-Glu 22 salt bridge.