Fmoc-Glu-NH

Base Information

• Chemical Name: Fmoc-Glu-NH
• CAS No.: 292150-20-0
• Molecular Formula: C20H20N2O5
• Molecular Weight: 368.389
• DSSTox Substance ID: DTXSID10435506
• Mol file: 292150-20-0.mol

Synonyms:292150-20-0;Fmoc-Glu-NH;Fmoc-Isogln-OH;Fmoc-isoglutamine;Fmoc-isogln;5-amino-4-(9H-fluoren-9-ylmethoxycarbonylamino)-5-oxopentanoic acid;267663-37-6;Fmoc-alpha-Glutamine;(4R)-5-amino-4-(9H-fluoren-9-ylmethoxycarbonylamino)-5-oxopentanoic acid;5-amino-4-[[9H-fluoren-9-ylmethoxy(oxo)methyl]amino]-5-oxopentanoic acid;DTXSID10435506;AKOS015918413;FT-0659350;A819818;S-292150-20-0;N~2~-{[(9H-Fluoren-9-yl)methoxy]carbonyl}-alpha-glutamine;4-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-5-amino-5-oxopentanoic acid;4-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-5-amino-5-oxopentanoicacid;5-amino-4-(9H-fluoren-9-ylmethoxycarbonylamino)-5-oxo-pentanoic acid;Fmoc-D-Glu-NH2

Chemical Property of Fmoc-Glu-NH

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Boiling Point: 687.715oC at 760 mmHg
• Flash Point: 369.717oC
• PSA: 123.20000
• Density: 1.332g/cm3
• LogP: 3.59790
• Storage Temp.: 2-8°C
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 8
• Exact Mass: 368.13722174
• Heavy Atom Count: 27
• Complexity: 545

Purity/Quality:

98%,99%, ^*data from raw suppliers

Fmoc-D-Glu-NH2 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)C(C3=CC=CC=C32)COC(=O)NC(CCC(=O)O)C(=O)N

Technology Process of Fmoc-Glu-NH

There total 12 articles about Fmoc-Glu-NH 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: 78.0%

N-Fmoc-D-glutamic acid (104091-09-0) → N-Fmoc-D-isoglutamine (292150-20-0)

Guidance literature:

N-Fmoc-D-glutamic acid; With dicyclohexyl-carbodiimide; In tetrahydrofuran; at 20 ℃; for 8h; Cooling with ice;

With ammonia; In tetrahydrofuran; for 1.5h; Cooling with ice;

Reference yield: 63.0%

C20H17NO5 (1286246-26-1) → N-Fmoc-D-isoglutamine (292150-20-0)

Guidance literature:

With ammonia; In tetrahydrofuran; at -10 ℃; for 1.5h;

DOI:10.1021/jm101577z

Reference yield:

D-Glutamic acid (6893-26-1,21675-62-7,23009-64-5,25104-13-6,84960-48-5,25513-46-6) → N-Fmoc-D-isoglutamine (292150-20-0)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 96 percent / aq. NaOH / 0.25 h / 60 °C

2.1: 1,3-dicyclohexylcarbodiimide / tetrahydrofuran / 7 h / cooling

2.2: 52.5 percent / NH₃(gas) / tetrahydrofuran / 0.5 h / cooling

3.1: H₂ / Pd/C / H₂O / 8 h / 20 °C / 2250.18 - 3000.24 Torr

4.1: 15.35 g / NaHCO₃ / acetone / 72 h / 20 °C

With sodium hydroxide; hydrogen; sodium hydrogencarbonate; dicyclohexyl-carbodiimide; palladium on activated charcoal; In tetrahydrofuran; water; acetone;

DOI:10.1021/jm0493313

upstream raw materials:

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide

D-α-glutamine

D-Glutamic acid

(R)-5-amino-4-(((benzyloxy)carbonyl)amino)-5-oxopentanoic acid

Downstream raw materials:

Nα-[4-chlorocinnamoyl-L-alanyl-D-isoglutaminyl]-L-lysine

Refernces

• 1、 Ma, Yao,Zhao, Nan,Liu, Gang. "Conjugate (MTC-220) of muramyl dipeptide analogue and paclitaxel prevents both tumor growth and metastasis in mice". . p. 2767 - 2777. Retrieved 2011/06/23.
• 2、 Liu, Gang,Zhang, Shuo-De,Xia, Shu-Quan,Ding, Zhen-Kai. "Solid-phase synthesis of muramyl dipeptide (MDP) derivatives using a multipin method". . p. 1361 - 1363. Retrieved 2007/10/03.