LHRH (1-5) (free acid)

Base Information

• Chemical Name: LHRH (1-5) (free acid)
• CAS No.: 52434-75-0
• Molecular Formula: C34H38 N8 O9
• Molecular Weight: 702.724
• European Community (EC) Number: 695-731-0
• ChEMBL ID: CHEMBL1866886
• Wikidata: Q76423087
• Mol file: 52434-75-0.mol

Synonyms:LHRH (1-5) (free acid);52434-75-0;(2S)-2-[[(2S)-3-hydroxy-2-[[(2S)-2-[[(2S)-3-(1H-imidazol-5-yl)-2-[[(2S)-5-oxopyrrolidine-2-carbonyl]amino]propanoyl]amino]-3-(1H-indol-3-yl)propanoyl]amino]propanoyl]amino]-3-(4-hydroxyphenyl)propanoic acid;pGlu-His-Trp-Ser-Tyr;Pyr-His-Trp-Ser-Tyr-OH;SCHEMBL8507206;CHEMBL1866886;L-Tyrosine, 5-oxo-L-prolyl-L-histidyl-L-tryptophyl-L-seryl-;NCGC00167306-01;(3S,6S,9S,12S)-3-((1H-imidazol-4-yl)methyl)-6-((1H-indol-3-yl)methyl)-12-(4-hydroxybenzyl)-9-(hydroxymethyl)-1,4,7,10-tetraoxo-1-((S)-5-oxopyrrolidin-2-yl)-2,5,8,11-tetraazatridecan-13-oic acid

Chemical Property of LHRH (1-5) (free acid)

Chemical Property:

• PSA: 267.73000
• LogP: 0.81160
• XLogP3: -0.1
• Hydrogen Bond Donor Count: 10
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 16
• Exact Mass: 702.27617482
• Heavy Atom Count: 51
• Complexity: 1260

Purity/Quality:

98%Min ^*data from raw suppliers

LHRH (1-5) 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC(=O)NC1C(=O)NC(CC2=CN=CN2)C(=O)NC(CC3=CNC4=CC=CC=C43)C(=O)NC(CO)C(=O)NC(CC5=CC=C(C=C5)O)C(=O)O
• Isomeric SMILES: C1CC(=O)N[C@@H]1C(=O)N[C@@H](CC2=CN=CN2)C(=O)N[C@@H](CC3=CNC4=CC=CC=C43)C(=O)N[C@@H](CO)C(=O)N[C@@H](CC5=CC=C(C=C5)O)C(=O)O

Technology Process of LHRH (1-5) (free acid)

There total 9 articles about LHRH (1-5) (free acid) which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

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

Guidance literature:

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

Reference yield:

Tyr(tBu) (16874-12-7,87553-74-0) → pGlu-His-Trp-Ser-Tyr (52434-75-0)

Guidance literature:

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

With methoxybenzene; trifluoroacetic acid; In 1,4-dioxane; methanol; water;

Reference yield:

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

Guidance literature:

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

With methoxybenzene; trifluoroacetic acid; In methanol; water;

upstream raw materials:

L-pyroglutamyl-L-histidyl-L-trypthophyl-L-seryl-L-tyrosine tert-butyl ester

O-benzyl-N-tert-butoxycarbonyl-L-tyrosine

BOC-O-benzyl-L-serine

Boc-Trp-OH

Downstream raw materials:

L-pyroglutamyl-L-histidyl-L-tryptophyl-L-seryl-L-tyrosyl-glycyl-L-leucyl-L-arginyl-L-prolyl-glycine amide hydrochloride

(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

L-pyroglutamyl-L-histidyl-L-tryptophyl-L-seryl-L-tyrosine methyl ester

Refernces

• 1、 Stetler-Stevenson, Mary Alice,Yang, Dai Chang,Lipkowski, Andrew,McCartney, Linda,Peterson, Darryl,Fluoret, George. "An Approach to the Elucidation of Metabolic Breakdown Products of the Luteinizing Hormone-Releasing Hormone". . p. 688 - 692. Retrieved 2007/10/02.