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L9761

Sigma-Aldrich

[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
MDL number:
MFCD00167541
UNSPSC Code:
12352209
PubChem Substance ID:
329817674
NACRES:
NA.32

assay

≥97% (HPLC)

form

powder

UniProt accession no.

P01148
P30968

storage temp.

−20°C

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

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

InChI key

VXKHXGOKWPXYNA-PGBVPBMZSA-N

Gene Information

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

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Amino Acid Sequence

Glp-His-Trp-Ser-Tyr-Trp-Leu-Arg-Pro-Gly-NH2

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_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
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
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.
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)
T Kádár et al.
Physiology & behavior, 51(3), 601-605 (1992-03-01)
The neuropharmacological actions of the agonist analog D-Trp-6-LH-RH were investigated in several tests after intracerebroventricular (ICV) administrations to male rats. The doses applied were 10, 100 and 1000 ng/animal. In the open field the 1000 ng ICV dose of the
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