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Acetyl-(Tyr1,D-Arg2)-GRF (1-29) amide (human)

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Acetyl-(D-Arg2)-GRF (1-29) amide (human) is a GRF antagonist.

Category

Peptide Inhibitors

Catalog number

BAT-015162

CAS number

93942-91-7

Molecular Formula

C154H255N47O43S

Molecular Weight

3485.03

Acetyl-(Tyr1,D-Arg2)-GRF (1-29) amide (human)

Specification
Reference Reading

IUPAC Name

(3S)-3-[[(2R)-2-[[(2S)-2-acetamido-3-(4-hydroxyphenyl)propanoyl]amino]-5-carbamimidamidopentanoyl]amino]-4-[[(2S)-1-[[(2S,3S)-1-[[(2S)-1-[[(2S,3R)-1-[[(2S)-4-amino-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-6-amino-1-[[(2S)-1-[[(2S)-1-[[2-[[(2S)-5-amino-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-6-amino-1-[[(2S)-1-[[(2S)-1-[[(2S)-5-amino-1-[[(2S)-1-[[(2S,3S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-amino-5-carbamimidamido-1-oxopentan-2-yl]amino]-3-hydroxy-1-oxopropan-2-yl]amino]-4-methylsulfanyl-1-oxobutan-2-yl]amino]-3-methyl-1-oxopentan-2-yl]amino]-3-carboxy-1-oxopropan-2-yl]amino]-1,5-dioxopentan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-1-oxohexan-2-yl]amino]-5-carbamimidamido-1-oxopentan-2-yl]amino]-1-oxopropan-2-yl]amino]-3-hydroxy-1-oxopropan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-1,5-dioxopentan-2-yl]amino]-2-oxoethyl]amino]-4-methyl-1-oxopentan-2-yl]amino]-3-methyl-1-oxobutan-2-yl]amino]-1-oxohexan-2-yl]amino]-5-carbamimidamido-1-oxopentan-2-yl]amino]-3-(4-hydroxyphenyl)-1-oxopropan-2-yl]amino]-3-hydroxy-1-oxopropan-2-yl]amino]-1,4-dioxobutan-2-yl]amino]-3-hydroxy-1-oxobutan-2-yl]amino]-1-oxo-3-phenylpropan-2-yl]amino]-3-methyl-1-oxopentan-2-yl]amino]-1-oxopropan-2-yl]amino]-4-oxobutanoic acid

Synonyms

Acetyl-(D-Arg2)-Sermorelin; Ac-Tyr-D-Arg-Asp-Ala-Ile-Phe-Thr-Asn-Ser-Tyr-Arg-Lys-Val-Leu-Gly-Gln-Leu-Ser-Ala-Arg-Lys-Leu-Leu-Gln-Asp-Ile-Met-Ser-Arg-NH2; N-acetyl-L-tyrosyl-D-arginyl-L-alpha-aspartyl-L-alanyl-L-isoleucyl-L-phenylalanyl-L-threonyl-L-asparagyl-L-seryl-L-tyrosyl-L-arginyl-L-lysyl-L-valyl-L-leucyl-glycyl-L-glutaminyl-L-leucyl-L-seryl-L-alanyl-L-arginyl-L-lysyl-L-leucyl-L-leucyl-L-glutaminyl-L-alpha-aspartyl-L-isoleucyl-L-methionyl-L-seryl-L-argininamide; [N-Acetyl-Tyr1, D-Arg2]-Growth Hormone Releasing Factor Fragment 1-29 amide human; 1-29-Somatoliberin (human pancreatic islet), N-acetyl-2-D-arginine-29-L-argininamide-; Somatoliberin (human pancreatic islet), N-acetyl-2-D-arginine-29-L-argininamide-30-de-L-glutamine-31-de-L-glutamine-32-deglycine-33-de-L-glutamic acid-34-de-L-serine-35-de-L-asparagine-36-de-L-glutamine-37-de-L-glutamic acid-38-de-L-arginine-39-deglycine-40-de-L-alanine-41-de-L-arginine-42-de-L-alanine-43-de-L-arginine-44-de-L-leucinamide-

Related CAS

93942-95-1 ((D-Arg2)-GRF (1-29) amide (human))

Appearance

White or Off-white Lyophilized Powder

Purity

95%

Density

1.45±0.1 g/cm3 (Predicted)

Sequence

Ac-YRDAIFTNSYRKVLGQLSARKLLQDIMSR-NH2

Storage

Store at -20°C

Solubility

Soluble in Water

InChI

InChI=1S/C154H255N47O43S/c1-20-80(13)120(199-125(219)83(16)174-135(229)108(69-117(213)214)190-130(224)96(40-32-59-172-154(167)168)182-139(233)104(176-85(18)206)66-87-41-45-89(207)46-42-87)149(243)193-106(65-86-33-23-22-24-34-86)142(236)201-122(84(17)205)150(244)194-107(68-115(159)211)141(235)197-112(74-204)146(240)189-105(67-88-43-47-90(208)48-44-88)140(234)183-95(39-31-58-171-153(165)166)128(222)181-93(36-26-28-55-156)134(228)198-119(79(11)12)147(241)192-100(61-75(3)4)126(220)173-71-116(212)177-97(49-51-113(157)209)131(225)187-103(64-78(9)10)138(232)196-110(72-202)144(238)175-82(15)124(218)179-94(38-30-57-170-152(163)164)127(221)180-92(35-25-27-54-155)129(223)186-102(63-77(7)8)137(231)188-101(62-76(5)6)136(230)184-98(50-52-114(158)210)132(226)191-109(70-118(215)216)143(237)200-121(81(14)21-2)148(242)185-99(53-60-245-19)133(227)195-111(73-203)145(239)178-91(123(160)217)37-29-56-169-151(161)162/h22-24,33-34,41-48,75-84,91-112,119-122,202-205,207-208H,20-21,25-32,35-40,49-74,155-156H2,1-19H3,(H2,157,209)(H2,158,210)(H2,159,211)(H2,160,217)(H,173,220)(H,174,229)(H,175,238)(H,176,206)(H,177,212)(H,178,239)(H,179,218)(H,180,221)(H,181,222)(H,182,233)(H,183,234)(H,184,230)(H,185,242)(H,186,223)(H,187,225)(H,188,231)(H,189,240)(H,190,224)(H,191,226)(H,192,241)(H,193,243)(H,194,244)(H,195,227)(H,196,232)(H,197,235)(H,198,228)(H,199,219)(H,200,237)(H,201,236)(H,213,214)(H,215,216)(H4,161,162,169)(H4,163,164,170)(H4,165,166,171)(H4,167,168,172)/t80-,81-,82-,83-,84+,91-,92-,93-,94-,95-,96+,97-,98-,99-,100-,101-,102-,103-,104-,105-,106-,107-,108-,109-,110-,111-,112-,119-,120-,121-,122-/m0/s1

InChI Key

JIFMAFJPNLVLAC-UBKPBUPGSA-N

Canonical SMILES

CCC(C)C(C(=O)NC(CC1=CC=CC=C1)C(=O)NC(C(C)O)C(=O)NC(CC(=O)N)C(=O)NC(CO)C(=O)NC(CC2=CC=C(C=C2)O)C(=O)NC(CCCNC(=N)N)C(=O)NC(CCCCN)C(=O)NC(C(C)C)C(=O)NC(CC(C)C)C(=O)NCC(=O)NC(CCC(=O)N)C(=O)NC(CC(C)C)C(=O)NC(CO)C(=O)NC(C)C(=O)NC(CCCNC(=N)N)C(=O)NC(CCCCN)C(=O)NC(CC(C)C)C(=O)NC(CC(C)C)C(=O)NC(CCC(=O)N)C(=O)NC(CC(=O)O)C(=O)NC(C(C)CC)C(=O)NC(CCSC)C(=O)NC(CO)C(=O)NC(CCCNC(=N)N)C(=O)N)NC(=O)C(C)NC(=O)C(CC(=O)O)NC(=O)C(CCCNC(=N)N)NC(=O)C(CC3=CC=C(C=C3)O)NC(=O)C

1. Plasma GH responses to human GHRH-antagonist in normal subjects

K Abe,A Tanaka,K Hanew,A Sugawara,A Utsumi Eur J Endocrinol . 1996 Jan;134(1):67-72. doi: 10.1530/eje.0.1340067.

The effect of GHRH-antagonist [(N-Ac-Tyr1, D-Arg2) GRF-(1-29)-NH2] on plasma GH morning and evening secretion was evaluated in 14 normal subjects (10 males, 4 females, aged 19-25 years). Plasma GH was determined using a high sensitivity IRMA kit (detection limit, 0.006 micrograms/l). After intravenous infusion of GHRH-antagonist (100 micrograms/100 ml saline over 75 min) in the morning, plasma GH remained constant during the 150 min post-infusion (N = 6). In contrast, when GHRH-antagonist was administered in the evening, plasma GH showed a clear and gradual decrease through the initial 90 min and returned to baseline levels at 150 min. Plasma GH values were also significantly lower from 75 min to 135 min when compared to physiological fluctuations in plasma GH (P < 0.05). Other anterior pituitary hormones remained unaffected by GHRH-antagonist. In conclusion, our data suggest that evening basal GH secretion, but not morning GH secretion, is maintained by endogenous GHRH.

2. Structural requirements for the activation of rat anterior pituitary adenylate cyclase by growth hormone-releasing factor (GRF): discovery of (N-Ac-Tyr1, D-Arg2)-GRF(1-29)-NH2 as a GRF antagonist on membranes

M L Heiman,J Christophe,M Waelbroeck,P Robberecht,P de Neef,J C Camus,D H Coy Endocrinology . 1985 Nov;117(5):1759-64. doi: 10.1210/endo-117-5-1759.

The efficacy and potency of 14 GH-releasing factor (GRF) analogs, substituted in position 1 to 7, on adenylate cyclase activation in crude homogenates from rat anterior pituitary were related to those of human pancreatic GRF(1-29)-amide and vasoactive intestinal peptide. Among several D-amino acid substitutions, that in position 2 was the only one to yield a super-agonist [with a Kact (concentration required for half-maximal adenylate cyclase activation) 2 times lower than that of GRF(1-29)-NH2]. By contrast, D-isomer substitution in position 1 and 3 was without effect and D-isomer substitution in position 4, 6, or 7 decreased the affinity of the analog. The N-acetylated analog of GRF was as potent and active as the parent peptide, and the identity of the amino acid in position 2 of (N-Ac-Tyr1)-GRF(1-29)-NH2 proved to be determining for enzyme activation, with D-Phe2 and D-Trp2 derivatives acting as partial agonists and the (N-Ac-Tyr1,D-Arg2) analog being an efficient competitive antagonist of GRF(1-29)-NH2. With use of this antagonist, it was possible to demonstrate that GRF and vasoactive intestinal peptide receptors represent distinct entities in the rat anterior pituitary.