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Tau Peptide (275-305) (Repeat 2 Domain)

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

Category

Functional Peptides

Catalog number

BAT-014720

CAS number

330456-25-2

Molecular Formula

C139H239N43O45S

Molecular Weight

3264.76

Specification
Reference Reading

IUPAC Name

(3S)-3-[[(2S)-6-amino-2-[[(2S)-2-[[2-[[(2R)-2-[[(2S)-6-amino-2-[[(2S)-2-[[(2S)-5-amino-2-[[(2S)-2-[[(2S)-4-amino-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-6-amino-2-[[(2S)-6-amino-2-[[(2S)-4-amino-2-[[(2S,3S)-2-[[(2S,3S)-2-[[(2S)-5-amino-2-[[(2S)-2-amino-3-methylbutanoyl]amino]-5-oxopentanoyl]amino]-3-methylpentanoyl]amino]-3-methylpentanoyl]amino]-4-oxobutanoyl]amino]hexanoyl]amino]hexanoyl]amino]-4-methylpentanoyl]amino]-3-carboxypropanoyl]amino]-4-methylpentanoyl]amino]-3-hydroxypropanoyl]amino]-4-oxobutanoyl]amino]-3-methylbutanoyl]amino]-5-oxopentanoyl]amino]-3-hydroxypropanoyl]amino]hexanoyl]amino]-3-sulfanylpropanoyl]amino]acetyl]amino]-3-hydroxypropanoyl]amino]hexanoyl]amino]-4-[[(2S)-4-amino-1-[[(2S,3S)-1-[[(2S)-6-amino-1-[[(2S)-1-[[(2S)-1-[(2S)-2-[[2-[[2-[[2-[[(1S)-1-carboxy-2-hydroxyethyl]amino]-2-oxoethyl]amino]-2-oxoethyl]amino]-2-oxoethyl]carbamoyl]pyrrolidin-1-yl]-3-methyl-1-oxobutan-2-yl]amino]-3-(1H-imidazol-5-yl)-1-oxopropan-2-yl]amino]-1-oxohexan-2-yl]amino]-3-methyl-1-oxopentan-2-yl]amino]-1,4-dioxobutan-2-yl]amino]-4-oxobutanoic acid

Synonyms

H-Val-Gln-Ile-Ile-Asn-Lys-Lys-Leu-Asp-Leu-Ser-Asn-Val-Gln-Ser-Lys-Cys-Gly-Ser-Lys-Asp-Asn-Ile-Lys-His-Val-Pro-Gly-Gly-Gly-Ser-OH; L-Valyl-L-glutaminyl-L-isoleucyl-L-isoleucyl-L-asparaginyl-L-lysyl-L-lysyl-L-leucyl-L-α-aspartyl-L-leucyl-L-seryl-L-asparaginyl-L-valyl-L-glutaminyl-L-seryl-L-lysyl-L-cysteinylglycyl-L-seryl-L-lysyl-L-α-aspartyl-L-asparaginyl-L-isoleucyl-L-lysyl-L-histidyl-L-valyl-L-prolylglycylglycylglycyl-L-serine

Appearance

White Powder

Purity

≥95%

Density

1.311±0.06 g/cm3

Boiling Point

2937.0±65.0°C at 760 mmHg

Sequence

VQIINKKLDLSNVQSKCGSKDNIKHVPGGGS

Storage

Store at -20°C

Solubility

Soluble in Acetic Acid, DMSO

InChI

InChI=1S/C139H239N43O45S/c1-17-71(14)110(135(222)164-79(35-24-29-45-144)117(204)168-84(49-74-55-151-65-156-74)126(213)178-109(70(12)13)138(225)182-46-30-36-95(182)132(219)155-57-102(193)152-56-101(192)153-58-103(194)158-93(63-186)139(226)227)180-128(215)87(52-100(149)191)169-125(212)88(53-105(196)197)171-116(203)77(33-22-27-43-142)161-129(216)90(60-183)157-104(195)59-154-113(200)94(64-228)176-118(205)78(34-23-28-44-143)162-130(217)91(61-184)174-119(206)80(37-39-96(145)187)165-134(221)108(69(10)11)177-127(214)86(51-99(148)190)170-131(218)92(62-185)175-122(209)83(48-67(6)7)167-124(211)89(54-106(198)199)172-121(208)82(47-66(4)5)166-115(202)76(32-21-26-42-141)159-114(201)75(31-20-25-41-140)160-123(210)85(50-98(147)189)173-136(223)111(72(15)18-2)181-137(224)112(73(16)19-3)179-120(207)81(38-40-97(146)188)163-133(220)107(150)68(8)9/h55,65-73,75-95,107-112,183-186,228H,17-54,56-64,140-144,150H2,1-16H3,(H2,145,187)(H2,146,188)(H2,147,189)(H2,148,190)(H2,149,191)(H,151,156)(H,152,193)(H,153,192)(H,154,200)(H,155,219)(H,157,195)(H,158,194)(H,159,201)(H,160,210)(H,161,216)(H,162,217)(H,163,220)(H,164,222)(H,165,221)(H,166,202)(H,167,211)(H,168,204)(H,169,212)(H,170,218)(H,171,203)(H,172,208)(H,173,223)(H,174,206)(H,175,209)(H,176,205)(H,177,214)(H,178,213)(H,179,207)(H,180,215)(H,181,224)(H,196,197)(H,198,199)(H,226,227)/t71-,72-,73-,75-,76-,77-,78-,79-,80-,81-,82-,83-,84-,85-,86-,87-,88-,89-,90-,91-,92-,93-,94-,95-,107-,108-,109-,110-,111-,112-/m0/s1

InChI Key

IHXTVVAJSPWVGI-YZBYVLPPSA-N

Canonical SMILES

CCC(C)C(C(=O)NC(C(C)CC)C(=O)NC(CC(=O)N)C(=O)NC(CCCCN)C(=O)NC(CCCCN)C(=O)NC(CC(C)C)C(=O)NC(CC(=O)O)C(=O)NC(CC(C)C)C(=O)NC(CO)C(=O)NC(CC(=O)N)C(=O)NC(C(C)C)C(=O)NC(CCC(=O)N)C(=O)NC(CO)C(=O)NC(CCCCN)C(=O)NC(CS)C(=O)NCC(=O)NC(CO)C(=O)NC(CCCCN)C(=O)NC(CC(=O)O)C(=O)NC(CC(=O)N)C(=O)NC(C(C)CC)C(=O)NC(CCCCN)C(=O)NC(CC1=CN=CN1)C(=O)NC(C(C)C)C(=O)N2CCCC2C(=O)NCC(=O)NCC(=O)NCC(=O)NC(CO)C(=O)O)NC(=O)C(CCC(=O)N)NC(=O)C(C(C)C)N

1. Specific binding of intravenous immunoglobulin products to tau peptide fragments

Lynnae M Smith, Mary P Coffey, David A Loeffler Int Immunopharmacol. 2014 Aug;21(2):279-82. doi: 10.1016/j.intimp.2014.05.009. Epub 2014 May 21.

The effects of intravenous immunoglobulin (IVIG) products are being evaluated in Alzheimer's disease (AD) patients. IVIG contains antibodies to tau protein, the main constituent of neurofibrillary tangles (NFTs). Tau has microtubule binding domain (MBD) repeats which are thought to be necessary for its aggregation, a key process in NFT formation. Tau's N-terminal region may also contribute to its aggregation and to the neurotoxicity of its soluble oligomers. This study examined the specific binding of IVIG products Gammagard, Gamunex, and Flebogamma to a tau N-terminal fragment (tau 45-73), tau's four MBD repeat sequences (tau 244-274, 275-305, 306-336, and 337-368), and a tau C-terminal fragment (tau 422-441). Mean antibody levels to tau 45-73 and tau 422-441 were significantly higher in Gamunex than in Gammagard and Flebogamma, while there were no significant differences between IVIG products for antibody concentrations to the MBD repeat sequences. Patterns of binding to tau fragments differed between IVIG products. Gammagard's highest binding was to tau 275-305 and tau 306-336 while Gamunex bound preferentially to tau 45-73 and tau 422-441. Flebogamma's binding to tau 275-305 and tau 306-336 was greater than to tau 337-368, and its binding to tau 306-336 was also higher than to tau 422-441. These findings indicate that IVIG products vary with respect to their binding to different regions of tau. This could result in differences with regard to their ability to prevent tau's aggregation and/or tau soluble oligomer neurotoxicity.

2. Mercury(II) promotes the in vitro aggregation of tau fragment corresponding to the second repeat of microtubule-binding domain: Coordination and conformational transition

Dan-Jing Yang, Shuo Shi, Leng-Feng Zheng, Tian-Ming Yao, Liang-Nian Ji Biopolymers. 2010 Dec;93(12):1100-7. doi: 10.1002/bip.21527.

The loss of metal homeostasis and the toxic effect of metal ion are important events in neurodegenerative and age-related diseases, such as Alzheimer's disease (AD). For the first time, we investigated the impacts of mercury(II) ions on the folding and aggregation of Alzheimer's tau fragment R2 (residues 275-305: VQIIN KKLDL SNVQS KCGSK DNIKH VPGGGS), corresponding to the second repeat unit of the microtubule-binding domain, which was believed to be pivotal to the biochemical properties of full tau protein. By ThS fluorescence assay and electron microscopy, we found that mercury(II) dramatically promoted heparin-induced aggregation of R2 at an optimum molar ratio of 1: 2 (metal: protein), and the resulting R2 filaments became smaller. Isothermal titration calorimetry (ITC) experiment revealed that the strong coordination of mercury(II) with R2 was an enthalpy-controlled, entropy-decreased thermodynamic process. The exceptionally large magnitude of heat release (ΔH₁ = -34.8 Kcal mol⁻¹) suggested that the most possible coordinating site on the R2 peptide chain was the thiol group of cysteine residue (Cys291), and this was further confirmed by a control experiment using Cys291 mutated R2. Circular dichroism spectrum demonstrated that this peptide underwent a significant conformational change from random coil to β-turn structure upon its binding to mercury(II) ion. This study was undertaken to better understand the mechanism of tau aggregation, and evaluate the possible role of mercury(II) in the pathogenesis of AD.