52434-75-0

Basic information

• Product Name: LHRH (1-5)
• Synonyms: LHRH (1-5);PGLU-HIS-TRP-SER-TYR;PYR-HIS-TRP-SER-TYR-OH;LHRH (1-5), free acid
• CAS NO: 52434-75-0
• Molecular Formula: C₃₄H₃₈N₈O₉
• Molecular Weight: 702.71
• Mol File: 52434-75-0.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: LHRH (1-5)(CAS DataBase Reference)
• NIST Chemistry Reference: LHRH (1-5)(52434-75-0)
• EPA Substance Registry System: LHRH (1-5)(52434-75-0)

Safety Data

• Hazardous Substances Data: 52434-75-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
LHRH (1-5) is used as a therapeutic agent for the treatment of hormone-related disorders and infertility. Its role in regulating the release of LH and FSH makes it a potential candidate for managing conditions such as precocious puberty, endometriosis, and certain types of infertility.
Used in Research Applications:
LHRH (1-5) is used as a research tool to study the mechanisms of reproductive function and the role of LHRH in the regulation of the hypothalamic-pituitary-gonadal axis. It helps researchers understand the molecular interactions and signaling pathways involved in the control of reproductive processes.
Used in Drug Development:
LHRH (1-5) is used in the development of synthetic analogs and drug delivery systems to improve the efficacy and targeted delivery of LHRH-based therapies. These analogs can be designed to have longer half-lives, increased stability, and enhanced receptor binding affinity, making them more effective in treating hormone-related disorders and infertility.

Synthetic route

L-pyroglutamyl-L-histidyl-L-trypthophyl-L-seryl-L-tyrosine tert-butyl ester (142822-22-8) → pGlu-His-Trp-Ser-Tyr (52434-75-0)

Conditions	Yield
With methoxybenzene; trifluoroacetic acid at 0℃; for 3h;

O-benzyl-N-tert-butoxycarbonyl-L-tyrosine (2130-96-3) + BOC-O-benzyl-L-serine (23680-31-1) + Boc-Trp-OH (13139-14-5) + Boc-His(Dnp)-OH (25024-53-7) + pGlu → pGlu-His-Trp-Ser-Tyr (52434-75-0)

Conditions	Yield
Yield given. Multistep reaction;

Tyr(tBu) (16874-12-7) → pGlu-His-Trp-Ser-Tyr (52434-75-0)

Conditions	Yield
Multi-step reaction with 4 steps 1: 78 percent / dioxane / 5 h / papain, dithioerythritol in phosphate buffer, pH 9 2: deprotection 3: 67 percent / methanol; H2O / 16 h / Ambient temperature; papain, dithioerythritol, pH 8 4: TFA, anisole / 3 h / 0 °C View Scheme

L-seryl-L-tyrosine tert-butyl ester (142822-21-7) → pGlu-His-Trp-Ser-Tyr (52434-75-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: 67 percent / methanol; H2O / 16 h / Ambient temperature; papain, dithioerythritol, pH 8 2: TFA, anisole / 3 h / 0 °C View Scheme

N-benzyloxycarbonyl-L-seryl-L-tyrosine tert-butyl ester (142822-20-6) → pGlu-His-Trp-Ser-Tyr (52434-75-0)

Conditions	Yield
Multi-step reaction with 3 steps 1: deprotection 2: 67 percent / methanol; H2O / 16 h / Ambient temperature; papain, dithioerythritol, pH 8 3: TFA, anisole / 3 h / 0 °C View Scheme

L-Pyroglutamyl-L-histidine Methyl Ester (25575-88-6) → pGlu-His-Trp-Ser-Tyr (52434-75-0)

Conditions	Yield
Multi-step reaction with 3 steps 1: 75 percent / CH2Cl2; H2O / 16 h / Ambient temperature; α-chymotrypsin 2: 67 percent / methanol; H2O / 16 h / Ambient temperature; papain, dithioerythritol, pH 8 3: TFA, anisole / 3 h / 0 °C View Scheme

L-tryptophanamide (20696-57-5) → pGlu-His-Trp-Ser-Tyr (52434-75-0)

Conditions	Yield
Multi-step reaction with 3 steps 1: 75 percent / CH2Cl2; H2O / 16 h / Ambient temperature; α-chymotrypsin 2: 67 percent / methanol; H2O / 16 h / Ambient temperature; papain, dithioerythritol, pH 8 3: TFA, anisole / 3 h / 0 °C View Scheme

L-pyroglutamyl-L-histidine-L-tryptophane amide (33217-51-5) → pGlu-His-Trp-Ser-Tyr (52434-75-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: 67 percent / methanol; H2O / 16 h / Ambient temperature; papain, dithioerythritol, pH 8 2: TFA, anisole / 3 h / 0 °C View Scheme

methanol (67-56-1) + pGlu-His-Trp-Ser-Tyr (52434-75-0) → L-pyroglutamyl-L-histidyl-L-tryptophyl-L-seryl-L-tyrosine methyl ester (51871-39-7)

Conditions	Yield
With boron trifluoride at 0℃; for 8h;	83%

pGlu-His-Trp-Ser-Tyr (52434-75-0) → (S)-2-{(S)-3-Hydroxy-2-[(Z)-2-{(S)-3-(1H-imidazol-4-yl)-2-[((S)-5-oxo-pyrrolidine-2-carbonyl)-amino]-propionylamino}-3-(1H-indol-3-yl)-acryloylamino]-propionylamino}-3-(4-hydroxy-phenyl)-propionic acid (207744-20-5)

Conditions	Yield
With (S)-tryptophan 2',3'-oxidase from Chromobacterium violaceum (ATCC 12472) In various solvent(s) at 30℃; for 20h;	66%

pGlu-His-Trp-Ser-Tyr (52434-75-0) → pGlu-His-[2',3'-2H]-Trp-Ser-Tyr

Conditions	Yield
Multi-step reaction with 2 steps 1: 66 percent / (S)-tryptophan 2',3'-oxidase from Chromobacterium violaceum (ATCC 12472) / various solvent(s) / 20 h / 30 °C 2: 95 percent / 2H2 / PdO / methanol / 20 h / 20 °C / 3800 Torr View Scheme

pGlu-His-Trp-Ser-Tyr (52434-75-0) → pGlu-His-[2',3'-2H]-(S)Trp-Ser-Tyr

Conditions	Yield
Multi-step reaction with 2 steps 1: 66 percent / (S)-tryptophan 2',3'-oxidase from Chromobacterium violaceum (ATCC 12472) / various solvent(s) / 20 h / 30 °C 2: 72 percent / 2H2 / / methanol / 20 h / 20 °C / 11400 Torr View Scheme

pGlu-His-Trp-Ser-Tyr (52434-75-0) → L-pyroglutamyl-L-histidyl-L-tryptophyl-L-seryl-L-tyrosyl-glycyl-L-leucyl-L-arginyl-L-prolyl-glycine amide hydrochloride (51952-40-0, 51952-41-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: 83 percent / 10percent BF3 / 8 h / 0 °C 2: 84 percent / dimethylformamide / 1 h / Ambient temperature; α-chymotrysin, 0.2M carbonate buffer, pH 8 View Scheme

Upstream product

• 142822-22-8 L-pyroglutamyl-L-histidyl-L-trypthophyl-L-seryl-L-tyrosine tert-butyl ester 
• 2130-96-3 O-benzyl-N-tert-butoxycarbonyl-L-tyrosine 
• 23680-31-1 BOC-O-benzyl-L-serine 
• 13139-14-5 Boc-Trp-OH 
• 25024-53-7 Boc-His(Dnp)-OH 
• 16874-12-7 Tyr(tBu) 
• 142822-20-6 N-benzyloxycarbonyl-L-seryl-L-tyrosine tert-butyl ester 
• 25575-88-6 L-Pyroglutamyl-L-histidine Methyl Ester 
• 33217-51-5 L-pyroglutamyl-L-histidine-L-tryptophane amide 
• 20696-57-5 L-tryptophanamide 
• 142822-21-7 L-seryl-L-tyrosine tert-butyl ester 

Downstream Products

• 51871-39-7 L-pyroglutamyl-L-histidyl-L-tryptophyl-L-seryl-L-tyrosine methyl ester 
• 207744-20-5 (S)-2-{(S)-3-Hydroxy-2-[(Z)-2-{(S)-3-(1H-imidazol-4-yl)-2-[((S)-5-oxo-pyrrolidine-2-carbonyl)-amino]-propionylamino}-3-(1H-indol-3-yl)-acryloylamino]-propionylamino}-3-(4-hydroxy-phenyl)-propionic acid 
• 51952-40-0 L-pyroglutamyl-L-histidyl-L-tryptophyl-L-seryl-L-tyrosyl-glycyl-L-leucyl-L-arginyl-L-prolyl-glycine amide hydrochloride 

Relevant articles and documents

Expedient Synthesis of Gonadotropin Releasing Hormone (GnRH) Through a Combined Chemical-Enzymatic Approach

We have developed a chemical-enzymatic synthetic approach to gonadotropin releasing hormone Glp1-His2-Trp3-Ser4-Tyr5-Gly6-Leu7-Arg8-Pro9-Gly10-NH2 (GnRH) which enables one to perform the synthesis efficiently according to minimal protection strategy with all reactive side chains of amino acids unprotected.Five peptide bonds His2-Trp3, Tyr5-Gly6, Leu7-Arg8 and Trp3-Ser4, Ser4-Tyr5 were formed by means of α-chymotrypsin and papain, respectively.The remaining four bonds Glp1-His2, Gly6-Leu7, Arg8-Pro9, Pro9-Gly10 were formed by chemical methods.The synthesis is simple to carry out and there are no problems in scaling up as demonstrated by the final coupling on 2 g scale affording highly pure GnRH in the yield of 84-90percent. Key Words: Gonadotropin Releasing Hormone, Enzymatic Peptide Synthesis, Papain, α-Chymotrypsin

An Approach to the Elucidation of Metabolic Breakdown Products of the Luteinizing Hormone-Releasing Hormone

Metabolic breakdown of the luteinizing hormone-releasing hormone (LH-RH) could lead to the following fragments containing pyroglutamic acid: pyroglutamic acid (1), pGlu-His (2), pGlu-His-Trp (3), pGlu-His-Trp-Ser (4), etc., and finally pGlu-His-Trp-Ser-Tyr-Gly-Leu-Arg-Pro-Gly (10).We have synthesized fragments 2-10 and successfully separated all ten metabolites and LH-RH by high-performance liquid chromatography (HPLC) with μBondapak C18 column.In a test of viability of the method, cochromatography of fragments 1-10 and LH-RH with the products of chymotryptic digestion of tritiated LH-RH showed radioactive peaks corresponding to the expected products, fragments 3 and 5.Analysis of the products of incubation of a rat kidney homogenate supernatant with LH-RH showed fragments 1-4 and LH-RH.The finding of breakdown at position 4 uncovers a new site of LH-RH breakdown and points the way to the design of potential LH-RH antagonists and agonists where the 4 position would be substituted with unnatural amino acids to prevent breakdown.