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L1898

Sigma-Aldrich

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

≥97% (HPLC)

Synonym(s):

(D-Ala-6) Luteinizing Hormone Releasing Hormone

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About This Item

Empirical Formula (Hill Notation):
C56H77N17O13 · xC2H4O2 · yH2O
Molecular Weight:
1196.32 (anhydrous free base basis)
UNSPSC Code:
12352209
PubChem Substance ID:
24896296

Quality Level

200

Assay

≥97% (HPLC)

composition

Peptide content, ≥65%

UniProt accession no.

P01148

storage temp.

−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

InChI key

KGUIXKYKIZMKMT-JGUOWLKQSA-N

Gene Information

human ... GNRH1(2796)

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Amino Acid Sequence

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

Application

[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 Actions

(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.

Pictograms

Health hazard
GHS08

Signal Word

Danger

Hazard Statements

H360

Precautionary Statements

P201 - P308 + P313

Hazard Classifications

Repr. 1B

Storage Class Code

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

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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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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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