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Merck

L9761

[D-Trp6]-LH-RH

≥97% (HPLC), powder

Synonym(s):

[D-Trp6]-Luteinizing hormone releasing hormone

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About This Item

Empirical Formula (Hill Notation):
C64H82N18O13
CAS Number:
57773-63-4
Molecular Weight:
1311.45
NACRES:
NA.32
PubChem Substance ID:
329817674
UNSPSC Code:
12352209
MDL number:
MFCD00167541

Key Documents

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Product Name

[D-Trp6]-LH-RH, ≥97% (HPLC), powder

InChI

1S/C64H82N18O13/c1-34(2)23-46(56(88)75-45(13-7-21-69-64(66)67)63(95)82-22-8-14-52(82)62(94)72-31-53(65)85)76-58(90)48(25-36-28-70-42-11-5-3-9-40(36)42)78-57(89)47(24-35-15-17-39(84)18-16-35)77-61(93)51(32-83)81-59(91)49(26-37-29-71-43-12-6-4-10-41(37)43)79-60(92)50(27-38-30-68-33-73-38)80-55(87)44-19-20-54(86)74-44/h3-6,9-12,15-18,28-30,33-34,44-52,70-71,83-84H,7-8,13-14,19-27,31-32H2,1-2H3,(H2,65,85)(H,68,73)(H,72,94)(H,74,86)(H,75,88)(H,76,90)(H,77,93)(H,78,89)(H,79,92)(H,80,87)(H,81,91)(H4,66,67,69)/t44-,45-,46-,47-,48+,49-,50-,51-,52-/m0/s1

SMILES string

CC(C)C[C@H](NC(=O)[C@@H](Cc1c[nH]c2ccccc12)NC(=O)[C@H](Cc3ccc(O)cc3)NC(=O)[C@H](CO)NC(=O)[C@H](Cc4c[nH]c5ccccc45)NC(=O)[C@H](Cc6c[nH]cn6)NC(=O)[C@@H]7CCC(=O)N7)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N8CCC[C@H]8C(=O)NCC(N)=O

InChI key

VXKHXGOKWPXYNA-PGBVPBMZSA-N

assay

≥97% (HPLC)

form

powder

UniProt accession no.

P01148
P30968

storage temp.

−20°C

Quality Level

200

Gene Information

human ... GNRH1(2796), GNRHR(2798)

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Application

[D-Trp6]-LH-RH (luteinizing hormone releasing hormone) has been used to study whether the (M. – X) region in electron capture dissociation provides information on amino acid composition of polypeptides. It is also used to study the effect of LH-RH on the production of progesterone (P), estradiol (E2) or human chorionic gonadotropin (hCG) by JEG-3 choriocarcinoma cells.

Biochem/physiol Actions

Potent LH-RH agonist with enhanced biological activity due to its slower rate of degradation. Like [D-Lys6]-LH-RH, the D-Trp6 analog has been shown to be effective against cancers expressing the LH-RH receptor. However, unlike the D-Lys6 analog, it is generally used in the unconjugated form.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

pictograms

Health hazard
GHS08

signalword

Danger

hcodes

H360

Hazard Classifications

Repr. 1B

Storage Class

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type P3 (EN 143) respirator cartridges

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Certificates of Analysis (COA)

Lot/Batch Number
BCCH1269
BCCB4898
BCBX4005
BCBT0543
BCBQ4733V

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Sandra Goericke-Pesch et al.
Theriogenology, 79(4), 640-646 (2012-12-26)
Although slow release GnRH-agonist implants have been shown to effectively suppress the estrous cycle in queens, there are still several remaining questions about their use: if the probability and frequency of estrus induction because of initial stimulation is dependent on
T Wolf et al.
Reproduction in domestic animals = Zuchthygiene, 47 Suppl 6, 387-388 (2013-01-04)
Four German Shorthair Pointer bitches each produced from two to five (total of 14) purebred litters in response to natural matings to either natural oestrus (n = 8) or oestrus induced by Ovuplant(®), a sustained-release implant containing 2.1 mg deslorelin
Colette Meyer et al.
Endocrine-related cancer, 20(1), 123-136 (2012-12-04)
GNRH significantly inhibits proliferation of a proportion of cancer cell lines by activating GNRH receptor (GNRHR)-G protein signaling. Therefore, manipulation of GNRHR signaling may have an under-utilized role in treating certain breast and ovarian cancers. However, the precise signaling pathways
Can the (M??X) Region in Electron Capture Dissociation Provide Reliable Information on Amino Acid Composition of Polypeptides?
Haselmann K F, et al.
Eur. J. Mass Spectrom., 8(6), 461-469 (2002)
C Maenhoudt et al.
Reproduction in domestic animals = Zuchthygiene, 47 Suppl 6, 393-397 (2013-01-04)
Over the last 10-15 years, long-acting GnRH agonists have become widely available. In the field of small animal reproduction, most recent studies have focused on the use of two compounds developed under the form of subcutaneous implants: azagly-nafarelin and deslorelin.
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