N-Cbz-D-Glutamine

Base Information

• Chemical Name: N-Cbz-D-Glutamine
• CAS No.: 13139-52-1
• Molecular Formula: C13H16N2O5
• Molecular Weight: 280.28
• Hs Code.: 29242990
• DSSTox Substance ID: DTXSID50365257
• Nikkaji Number: J304.867E
• Wikidata: Q72441971
• Mol file: 13139-52-1.mol

Synonyms:13139-52-1;Z-D-Gln-OH;N-Cbz-D-Glutamine;Z-D-glutamine;(2R)-5-amino-5-oxo-2-(phenylmethoxycarbonylamino)pentanoic acid;((Benzyloxy)carbonyl)-D-glutamine;(2R)-2-{[(BENZYLOXY)CARBONYL]AMINO}-4-CARBAMOYLBUTANOIC ACID;Cbz-D-glutamine;MFCD00065698;(R)-5-Amino-2-(((benzyloxy)carbonyl)amino)-5-oxopentanoic acid;N-carbobenzoxy-D-glutamine;SCHEMBL3509748;DTXSID50365257;JIMLDJNLXLMGLX-SNVBAGLBSA-N;AKOS016842890;FD21565;AC-17140;AS-49121;Z-D-Gln-OH, >=98.0% (HPLC);CS-0169150;D-Glutamine, N2-[(phenylmethoxy)carbonyl]-;EN300-6503937;A888494;N-alpha-BenZyloxycarbonyl-D-glutamine (CbZ-D-Gln-OH);(R)-2-[[(Benzyloxy)carbonyl]amino]-4-carbamoylbutyric acid

Chemical Property of N-Cbz-D-Glutamine

Chemical Property:

• Vapor Pressure: 1.9E-15mmHg at 25°C
• Melting Point: 138-142°C
• Refractive Index: 1.565
• Boiling Point: 604.2 °C at 760 mmHg
• PKA: 3.82±0.10(Predicted)
• Flash Point: 319.2 °C
• PSA: 118.72000
• Density: 1.316 g/cm³
• LogP: 1.72270
• Storage Temp.: Store at RT.
• XLogP3: 0.3
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 8
• Exact Mass: 280.10592162
• Heavy Atom Count: 20
• Complexity: 353

Purity/Quality:

99% ^*data from raw suppliers

N2-Cbz-D-glutamine ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)COC(=O)NC(CCC(=O)N)C(=O)O
• Isomeric SMILES: C1=CC=C(C=C1)COC(=O)N[C@H](CCC(=O)N)C(=O)O
• Uses: N2-Cbz-D-glutamine is an N-Cbz-protected form of D-Glutamine (G597295). D-Glutamine is an unnatural isomer of L-Glutamine (G597000) that is present in human plasma an is a source of liberated ammonia. D-Glutamine can be synthesized by enzymatic means or can be found in cheeses, wine and vinegars as well. It is often used to determine the activity of Glutamine synthetase, an enzyme that is commonly found in the mammalian liver and brain that controls the use of nitrogen in cells.

Technology Process of N-Cbz-D-Glutamine

There total 1 articles about N-Cbz-D-Glutamine 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: 89.0%

ethanol (64-17-5) + Nα-benzyloxycarbonyl-glutamine (50516-14-8) → N-carbobenzoxy-D-glutamine (13139-52-1) + N2-benzyloxycarbonyl-l-glutamine ethyl ester (4668-41-1)

Guidance literature:

With citrate buffer; DL-cysteine hydrochloride; papain; at 50 ℃; for 24h;

Reference yield: 77.0%

N-carbobenzoxy-D-glutamine (13139-52-1) → benzyloxycarbonyl-D-glutamic acid diamide (76491-40-2)

Guidance literature:

N-carbobenzoxy-D-glutamine; With chloroformic acid ethyl ester; triethylamine; In tetrahydrofuran; at 0 ℃; for 0.5h;

With ammonium chloride; In tetrahydrofuran; water; at 0 ℃; for 0.5h;

DOI:10.1016/j.tetasy.2017.10.015

Reference yield:

N-carbobenzoxy-D-glutamine (13139-52-1) → (R)-3-N-Cbz-amino-2,6-dioxopiperidine (179915-11-8)

Guidance literature:

With 1-hydroxy-pyrrolidine-2,5-dione; dicyclohexyl-carbodiimide; In DMF (N,N-dimethyl-formamide);

upstream raw materials:

ethanol

Nα-benzyloxycarbonyl-glutamine

Downstream raw materials:

[(R)-3-Carbamoyl-1-(piperidine-1-carbonyl)-propyl]-carbamic acid benzyl ester

[(R)-3-Amino-1-(piperidine-1-carbonyl)-propyl]-carbamic acid benzyl ester

[(R)-1-(Piperidine-1-carbonyl)-3-(2,3,5,6-tetrachloro-pyridin-4-ylamino)-propyl]-carbamic acid benzyl ester

(R)-3-N-Cbz-amino-2,6-dioxopiperidine

Refernces