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L1898

Sigma-Aldrich

[D-Ala6]-LH-RH acetate salt hydrate

≥97% (HPLC)

Synonym(e):

(D-Ala-6) Luteinizing Hormone Releasing Hormone

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About This Item

Empirische Formel (Hill-System):
C56H77N17O13 · xC2H4O2 · yH2O
Molekulargewicht:
1196.32 (anhydrous free base basis)
UNSPSC-Code:
12352209
PubChem Substanz-ID:
24896296
NACRES:
NA.77

Assay

≥97% (HPLC)

Zusammensetzung

Peptide content, ≥65%

UniProt-Hinterlegungsnummer

P01148

Lagertemp.

−20°C

SMILES String

[H]O[H].CC(O)=O.CC(C)C[C@H](NC(=O)[C@@H](C)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@H](CO)NC(=O)[C@H](Cc2c[nH]c3ccccc23)NC(=O)[C@H](Cc4cnc[nH]4)NC(=O)[C@@H]5CCC(=O)N5)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N6CCC[C@H]6C(=O)NCC(N)=O

InChI

1S/C56H77N17O13.C2H4O2.H2O/c1-29(2)20-39(50(81)67-38(10-6-18-61-56(58)59)55(86)73-19-7-11-44(73)54(85)63-26-45(57)76)68-47(78)30(3)65-49(80)40(21-31-12-14-34(75)15-13-31)69-53(84)43(27-74)72-51(82)41(22-32-24-62-36-9-5-4-8-35(32)36)70-52(83)42(23-33-25-60-28-64-33)71-48(79)37-16-17-46(77)66-37;1-2(3)4;/h4-5,8-9,12-15,24-25,28-30,37-44,62,74-75H,6-7,10-11,16-23,26-27H2,1-3H3,(H2,57,76)(H,60,64)(H,63,85)(H,65,80)(H,66,77)(H,67,81)(H,68,78)(H,69,84)(H,70,83)(H,71,79)(H,72,82)(H4,58,59,61);1H3,(H,3,4);1H2/t30-,37+,38+,39+,40+,41+,42+,43+,44+;;/m1../s1

InChIKey

KGUIXKYKIZMKMT-JGUOWLKQSA-N

Angaben zum Gen

human ... GNRH1(2796)

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Amino Acid Sequence

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

Anwendung

[D-Ala6]-LH-RH acetate salt hydrate has been used to induce ovulation and to synchronize the reproductive cycle in Sprague-Dawley female rats.

Biochem./physiol. Wirkung

(D-Ala6)-LH-RH is a GnRH (gonadotropin-releasing hormone) agonist. GnRH, which is also referred to as LHRH (luteinizing hormone-releasing hormone) or gonadorelin, is crucial for mammalian reproduction and is released from hypothalamic neurons. It is responsible for the secretion of gonadotropins, luteinizing hormone (LH) and follicle-stimulating hormone (FSH), from pituitary glands. Mutations in GnRH are associated with normosmic congenital hypogonadotropic hypogonadism.
Potent LH-RH agonist.

Piktogramme

Health hazard
GHS08

Signalwort

Danger

H-Sätze

H360

Gefahreneinstufungen

Repr. 1B

Lagerklassenschlüssel

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

WGK

WGK 3

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable

Persönliche Schutzausrüstung

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

Analysenzertifikate (COA)

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J Chen et al.
Journal of neuroendocrinology, 24(7), 1055-1064 (2012-03-02)
Exposure to stress during early development causes long-lasting alterations in behaviour and hypothalamic pituitary adrenal (HPA) axis activity, including increased expression of corticotrophin-releasing hormone (CRH). To determine whether early-life stress causes epigenetic changes in the CRH promoter leading to increased
Luigi Maione et al.
PloS one, 8(7), e69616-e69616 (2013-08-13)
Normosmic congenital hypogonadotropic hypogonadism (nCHH) is a rare reproductive disease leading to lack of puberty and infertility. Loss-of-function mutations of GNRH1 gene are a very rare cause of autosomal recessive nCHH. R31C GNRH1 is the only missense mutation that affects
Indira Nederpelt et al.
British journal of pharmacology, 173(1), 128-141 (2015-09-24)
Drug-target residence time is an important, yet often overlooked, parameter in drug discovery. Multiple studies have proposed an increased residence time to be beneficial for improved drug efficacy and/or longer duration of action. Currently, there are many drugs on the
Brooke Tata et al.
PLoS biology, 12(9), e1001952-e1001952 (2014-09-24)
Characterization of the genetic defects causing gonadotropic deficiency has made a major contribution to elucidation of the fundamental role of Kisspeptins and Neurokinin B in puberty onset and reproduction. The absence of puberty may also reveal neurodevelopmental disorders caused by

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