(D-SER4)-GONADORELIN

Base Information

• Chemical Name: (D-SER4)-GONADORELIN
• CAS No.: 103065-82-3
• Molecular Formula: C₅₅H₇₅N₁₇O₁₃
• Molecular Weight: 1182.31
• Mol file: 103065-82-3.mol

Synonyms:(D-SER4)-GONADORELIN;(D-SER4)-GONADOTROPIN-RELEASING HORMONE;(D-SER4)-LHRH;[D-SER4]-LH-RH [D-SER4]-GONADORELIN;(D-SER4)-LUTEINIZING HORMONE-RELEASING FACTOR;(D-SER4)-LUTEINIZING HORMONE-RELEASING HORMONE;PYR-HIS-TRP-D-SER-TYR-GLY-LEU-ARG-PRO-GLY-NH2

Chemical Property of (D-SER4)-GONADORELIN

Chemical Property:

• PSA: 472.13000
• LogP: 1.10740
• Storage Temp.: −20°C

Purity/Quality:

99%+, ^*data from raw suppliers

[D-SER4]-LH-RH 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (D-SER4)-GONADORELIN

There total 20 articles about (D-SER4)-GONADORELIN 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:

N-(fluoren-9-ylmethoxycarbonyl)glycine (29022-11-5) + Fmoc-Leu-OH (35661-60-0) + Fmoc-Pro-OH (71989-31-6) + Fmoc-Ser(tBu)-OH (71989-33-8) + Fmoc-Tyr(tBu)-OH (71989-38-3,118488-18-9,204384-67-8) + Fmoc-His(Trt)-OH (109425-51-6) + N-fluoren-9-ylmethyloxycarbonyl-L-pyroglutamine (109425-56-1,106982-77-8) + 3-[(S)-2-carboxy-2-(9H-fluoren-9-ylmethoxycarbonylamino)ethyl]indole-1-carboxylic acid tert-butyl ester (143824-78-6,163619-04-3) + Nα-(9-fluorenylmethyloxycarbonyl)-Nγ-2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl-L-arginine (187618-60-6) → gonadotropin releasing hormone (33515-09-2,51988-59-1,53634-19-8,53634-20-1,53634-21-2,53634-22-3,53728-75-9,64693-15-8,70920-45-5,103065-82-3)

Guidance literature:

N-(fluoren-9-ylmethoxycarbonyl)glycine; With N-ethyl-N,N-diisopropylamine; at 90 ℃; for 0.0833333h; Automated synthesizer;

With pyrrolidine; at 95 ℃; for 0.0138889h;

N-(fluoren-9-ylmethoxycarbonyl)glycine; Fmoc-Leu-OH; Fmoc-Pro-OH; Fmoc-Ser(tBu)-OH; Fmoc-Tyr(tBu)-OH; Fmoc-His(Trt)-OH; N-fluoren-9-ylmethyloxycarbonyl-L-pyroglutamine; 3-[(S)-2-carboxy-2-(9H-fluoren-9-ylmethoxycarbonylamino)ethyl]indole-1-carboxylic acid tert-butyl ester; Nα-(9-fluorenylmethyloxycarbonyl)-Nγ-2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl-L-arginine; Further stages;

Reference yield:

BOC-glycine (4530-20-5) + 1-(tert-butoxycarbonyl)-L-proline (15761-39-4,59433-50-0) + N-tert-butoxycarbonyl-L-leucine (13139-15-6,53296-34-7) + C14H14NPol + Boc-Arg(Tos)-OH (13836-37-8) + BOC-O-benzyl-L-serine (23680-31-1) + (S)-3-[4-(2-Bromo-benzyloxycarbonyloxy)-phenyl]-2-tert-butoxycarbonylamino-propionic acid (47689-67-8) + Nα-tert-butoxycarbonyl-1-formyl-L-tryptophan (47355-10-2) + L-N-t-butoxycarbonylpyroglutamic acid (53100-44-0,160347-90-0) + Boc-His(Tos)-OH (35899-43-5) → gonadotropin releasing hormone (33515-09-2,51988-59-1,53634-19-8,53634-20-1,53634-21-2,53634-22-3,53728-75-9,64693-15-8,70920-45-5,103065-82-3)

Guidance literature:

BOC-glycine; C₁₄H₁₄NPol; With benzotriazol-1-ol; diisopropyl-carbodiimide; In N,N-dimethyl-formamide; solid phase reaction;

With trifluoroacetic acid; In dichloromethane; for 0.5h; solid phase reaction;

BOC-glycine; 1-(tert-butoxycarbonyl)-L-proline; N-tert-butoxycarbonyl-L-leucine; Boc-Arg(Tos)-OH; BOC-O-benzyl-L-serine; (S)-3-[4-(2-Bromo-benzyloxycarbonyloxy)-phenyl]-2-tert-butoxycarbonylamino-propionic acid; Nα-tert-butoxycarbonyl-1-formyl-L-tryptophan; L-N-t-butoxycarbonylpyroglutamic acid; Boc-His(Tos)-OH; Further stages;

DOI:10.1016/j.bioorg.2011.01.001

Reference yield:

N5-[imino(nitroamino)methyl]-N2-[(phenylmethoxy)carbonyl]-L-ornithine (2304-98-5) → gonadotropin releasing hormone (33515-09-2,51988-59-1,53634-19-8,53634-20-1,53634-21-2,53634-22-3,53728-75-9,64693-15-8,70920-45-5,103065-82-3)

Guidance literature:

Multi-step reaction with 7 steps

1: 84 percent / 1-hydroxybenzotriazol hydrate, triethylamine, DCC / dimethylformamide / 1) 2.5h, 0 deg C, 2) 17h, RT

2: 94 percent / 25percent HBr/acetic acid / 0.58 h / 30 °C

3: 83 percent / triethylamine / dioxane / 1)3h, Et₃N, 2) 25h, RT, 1n HCl

4: 97 percent / 1n NaOH, H₂O / dioxane / 3 h / Ambient temperature

5: 86 percent / N-methylmorpholine, isobutyl chlorocarbonate, triethylamine / dimethylformamide / 1) 1h, 0 deg C, 2) 4h, RT

6: 93 percent / N₂ / palladium black / 1 h / Ambient temperature

7: 1) 6.1n HCl, isoamyl nitrite, 2) triethylamine / 1) -30deg C, THF, 30 min; 2) -45deg C, DMF, 15h between -5deg C to 0deg C

With 4-methyl-morpholine; hydrogenchloride; sodium hydroxide; nitrogen; water; hydrogen bromide; acetic acid; 1-hydroxybenzotriazol-hydrate; triethylamine; dicyclohexyl-carbodiimide; isobutyl chloroformate; isopentyl nitrite; palladium; In 1,4-dioxane; N,N-dimethyl-formamide;

upstream raw materials:

L-Leucyl-L-arginyl-L-prolylglycinamide Formate

L-Pyroglutamyl-L-histidyl-L-tryptophyl-L-seryl-L-tyrosylglycine Hydrazine

N₅-[imino(nitroamino)methyl]-N₂-[(phenylmethoxy)carbonyl]-L-ornithine

N^α-tert-butoxycarbonylseryltyrosine methyl ester

Downstream raw materials:

L-histidyl-L-tryptophanyldiketopiperazine

pGlu-His-Trp-Ser-Tyr-Gly-Leu-Arg-Pro-Gly-OH

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

Refernces

• 1、 Nakaie, Clovis R.,Oliveira, Eliandre,Vicente, Eduardo F.,Jubilut, Guita N.,Souza, Sinval E.G.,Marchetto, Reinaldo,Cilli, Eduardo M.. "Solid-phase peptide synthesis in highly loaded conditions". experimental part. p. 101 - 109. Retrieved 2011/06/25.
• 2、 Rzeszotarska, Barbara,Masiukiewicz, Elzbieta,Kmiecik-Chmura, Halina. "Synthesis of Gonadoliberin, a Gonadotropin Releasing Hormone". . p. 791 - 798. Retrieved 2007/10/02.