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(Asp76)-pTH (39-84) (human)

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Asp76-pTH (39-84) (human) is a synthetic peptide widely utilized in the biomedical sector exhibiting its prowess as a potent receptor antagonist for parathyroid hormone (PTH), exerting pivotal influence over the intricate dynamics of calcium and phosphate metabolism.

Category

Peptide Inhibitors

Catalog number

BAT-015240

CAS number

79804-72-1

Molecular Formula

C211H356N66O73

Molecular Weight

4985.55

Specification
Reference Reading

IUPAC Name

(4S)-4-[[(2S)-6-amino-2-[[(2S)-6-amino-2-[[(2S)-2-[[(2S)-1-[(2S)-2-[[(2S)-5-amino-2-[[(2S)-2-[[2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-1-[(2S)-2-[[(2S)-2-[[(2S)-1-[(2S)-2-aminopropanoyl]pyrrolidine-2-carbonyl]amino]-4-methylpentanoyl]amino]propanoyl]pyrrolidine-2-carbonyl]amino]-5-carbamimidamidopentanoyl]amino]-3-carboxypropanoyl]amino]propanoyl]amino]acetyl]amino]-3-hydroxypropanoyl]amino]-5-oxopentanoyl]amino]-5-carbamimidamidopentanoyl]pyrrolidine-2-carbonyl]amino]-5-carbamimidamidopentanoyl]amino]hexanoyl]amino]hexanoyl]amino]-5-[[(2S)-1-[[(2S)-4-amino-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-6-amino-1-[[(2S)-1-[[(2S)-1-(carboxymethylamino)-4-methyl-1-oxopentan-2-yl]amino]-3-hydroxy-1-oxopropan-2-yl]amino]-1-oxohexan-2-yl]amino]-4-carboxy-1-oxobutan-2-yl]amino]-3-(1H-imidazol-4-yl)-1-oxopropan-2-yl]amino]-3-hydroxy-1-oxopropan-2-yl]amino]-4-carboxy-1-oxobutan-2-yl]amino]-3-methyl-1-oxobutan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-3-methyl-1-oxobutan-2-yl]amino]-1,4-dioxobutan-2-yl]amino]-3-carboxy-1-oxopropan-2-yl]amino]-5-oxopentanoic acid

Synonyms

H-Ala-Pro-Leu-Ala-Pro-Arg-Asp-Ala-Gly-Ser-Gln-Arg-Pro-Arg-Lys-Lys-Glu-Asp-Asn-Val-Leu-Val-Glu-Ser-His-Glu-Lys-Ser-Leu-Gly-Glu-Ala-Asp-Lys-Ala-Asp-Val-Asp-Val-Leu-Thr-Lys-Ala-Lys-Ser-Gln-OH; 39-84-Parathormone (human); L-Alanyl-L-prolyl-L-leucyl-L-alanyl-L-prolyl-L-arginyl-L-α-aspartyl-L-alanylglycyl-L-seryl-L-glutaminyl-L-arginyl-L-prolyl-L-arginyl-L-lysyl-L-lysyl-L-α-glutamyl-L-α-aspartyl-L-asparaginyl-L-valyl-L-leucyl-L-valyl-L-α-glutamyl-L-seryl-L-histidyl-L-α-glutamyl-L-lysyl-L-seryl-L-leucylglycyl-L-α-glutamyl-L-alanyl-L-α-aspartyl-L-lysyl-L-alanyl-L-α-aspartyl-L-valyl-L-α-aspartyl-L-valyl-L-leucyl-L-threonyl-L-lysyl-L-alanyl-L-lysyl-L-seryl-L-glutamine; human parathormone (39-84)

Appearance

White Lyophilized Powder

Purity

≥95% by HPLC

Sequence

APLAPRDAGSQRPRKKEDNVLVESHEKSLGEADKADVDVLTKAKSQ

Storage

Store at -20°C

Solubility

Soluble in Water

InChI

InChI=1S/C139H234N46O46/c1-66(2)52-85(110(205)157-61-106(202)203)172-127(222)93(63-187)179-115(210)77(28-16-19-45-142)164-116(211)81(36-40-101(192)193)166-122(217)88(55-74-59-152-65-158-74)173-128(223)94(64-188)180-119(214)83(38-42-103(196)197)170-132(227)107(69(7)8)181-124(219)87(54-68(5)6)178-133(228)108(70(9)10)182-125(220)89(56-99(145)190)174-123(218)91(58-105(200)201)176-118(213)82(37-41-102(194)195)165-112(207)76(27-15-18-44-141)162-111(206)75(26-14-17-43-140)163-113(208)78(29-20-46-153-137(146)147)168-130(225)97-34-25-51-185(97)136(231)84(31-22-48-155-139(150)151)171-117(212)80(35-39-98(144)189)167-126(221)92(62-186)161-100(191)60-156-109(204)72(12)159-121(216)90(57-104(198)199)175-114(209)79(30-21-47-154-138(148)149)169-129(224)96-33-24-50-184(96)135(230)73(13)160-120(215)86(53-67(3)4)177-131(226)95-32-23-49-183(95)134(229)71(11)143/h59,65-73,75-97,107-108,186-188H,14-58,60-64,140-143H2,1-13H3,(H2,144,189)(H2,145,190)(H,152,158)(H,156,204)(H,157,205)(H,159,216)(H,160,215)(H,161,191)(H,162,206)(H,163,208)(H,164,211)(H,165,207)(H,166,217)(H,167,221)(H,168,225)(H,169,224)(H,170,227)(H,171,212)(H,172,222)(H,173,223)(H,174,218)(H,175,209)(H,176,213)(H,177,226)(H,178,228)(H,179,210)(H,180,214)(H,181,219)(H,182,220)(H,192,193)(H,194,195)(H,196,197)(H,198,199)(H,200,201)(H,202,203)(H4,146,147,153)(H4,148,149,154)(H4,150,151,155)/t71-,72-,73-,75-,76-,77-,78-,79-,80-,81-,82-,83-,84-,85-,86-,87-,88-,89-,90-,91-,92-,93-,94-,95-,96-,97-,107-,108-/m0/s1

InChI Key

PMNYRRYRKDDSKY-DEGCQRHESA-N

Canonical SMILES

CC(C)CC(C(=O)NC(C)C(=O)N1CCCC1C(=O)NC(CCCNC(=N)N)C(=O)NC(CC(=O)O)C(=O)NC(C)C(=O)NCC(=O)NC(CO)C(=O)NC(CCC(=O)N)C(=O)NC(CCCNC(=N)N)C(=O)N2CCCC2C(=O)NC(CCCNC(=N)N)C(=O)NC(CCCCN)C(=O)NC(CCCCN)C(=O)NC(CCC(=O)O)C(=O)NC(CC(=O)O)C(=O)NC(CC(=O)N)C(=O)NC(C(C)C)C(=O)NC(CC(C)C)C(=O)NC(C(C)C)C(=O)NC(CCC(=O)O)C(=O)NC(CO)C(=O)NC(CC3=CNC=N3)C(=O)NC(CCC(=O)O)C(=O)NC(CCCCN)C(=O)NC(CO)C(=O)NC(CC(C)C)C(=O)NCC(=O)O)NC(=O)C4CCCN4C(=O)C(C)N

1. Biological properties of synthetic human parathyroid hormone: effect of deamidation at position 76 on agonist and antagonist activity

S Sakakibara, G Zaman, T Kimura, N Loveridge, G N Hendy, P W Saphier, S M Bernier Endocrinology . 1991 May;128(5):2583-90. doi: 10.1210/endo-128-5-2583.

Recent studies have suggested a role for the carboxyl-terminus of PTH in the binding of the molecule to renal and skeletal receptors, but the functional significance of this binding remains uncertain. We have investigated the possible role of this region by examining the effect of substituting the asparagine residue at position 76 of the native human molecule [Asn76]hPTH-(1-84) with an aspartate residue, [Asp76] hPTH-(1-84) on activity in both renal and skeletal cytochemical (CBA) and adenylate cyclase (AC) bioassays. In the renal CBA, [Asp76]hPTH-(1-84) was considerably less potent than [Asn76]hPTH-(1-84) and produced dose-dependent inhibition of the bioactivity of intact bovine (b) PTH-(1-84), bPTH-(1-34), and [Asn76]hPTH-(1-84). [Asp76]hPTH-(39-84) inhibited the response to intact PTH to a lesser extent, whereas [Asp76]hPTH-(53-84) had no antagonistic activity. In the metatarsal CBA, [Asp76]hPTH-(1-84) inhibited the response to intact PTH, but was less potent than in the renal CBA. In both renal (OK) and skeletal (UMR) cell AC assays [Asp76]hPTH-(1-84) and [Asn76]hPTH-(1-84) were equipotent agonists. Therefore, the CBAs are much more sensitive to modification of the carboxyl end of the molecule than AC assays. The antagonist properties of [Asp76]hPTH-(1-84) appeared to be mediated by phosphodiesterase activation as theophylline abolished the antagonism of this analog. These studies indicate that generation of PTH analogs, modified at the carboxyl-terminal region as well as at the amino-terminus, may be useful for developing potent PTH antagonists.