Cas no 15387-45-8 (Boc-Gln-ONp)
Boc-Gln-ONp Chemical and Physical Properties
Names and Identifiers
-
- 2-tert-Butoxycarbonylamino-4-carbamoylbutyric acid 4-nitrophenyl ester
- Boc-Gln-ONp
- 4 weeks
- Boc-Gln-Op
- Boc-L-Gln-ONp
- Boc-L-glutamine p-nitrophenylester
- 4-nitrophenyl ester
- Boc-Gin-ONp
- Boc-Gln-(4-Nitrophenyl)OH
- BOC-GLUTAMINE-ONP
- Boc-L-Gln.Onp
- BOC-L-GLUTAMINE 4-NITROPHENYL ESTER
- L-Boc-Gln-ONp
- L-Boc-Gln-OPNP
- N-tert-butoxycarbonyl-glutamine p-nitrophenyl ester
- N-tert-butyloxycarbonyl-glutamine p-nitrophenyl ester
- N-α-Boc-L-glutamine 4-nitrophenyl ester
- BOC-GLN-ONPBOC-G
- (Tert-Butoxy)Carbonyl Gln-ONp
- 4-nitrophenyl ester
- BOC-L-GLUTAMINE P-NITROPHENYL ESTER
- 4-Nitrophenyl (tert-butoxycarbonyl)-L-glutaminate
- SCHEMBL7385206
- 15387-45-8
- L-Glutamine, N2-((1,1-dimethylethoxy)carbonyl)-, 4-nitrophenyl ester
- Boc-Gln-ONp, >=98.0% (HPLC)
- FD21536
- A-Boc-L-glutamine 4-nitrophenyl ester
- AKOS015833422
- AM81765
- L-Glutamine, N2-[(1,1-dimethylethoxy)carbonyl]-, 4-nitrophenyl ester
- (S)-4-NITROPHENYL 5-AMINO-2-((TERT-BUTOXYCARBONYL)AMINO)-5-OXOPENTANOATE
- AS-49110
- DTXSID30884835
- MFCD00065572
- HJMMCTZLXOVMFB-LBPRGKRZSA-N
- (4-nitrophenyl) (2S)-5-amino-2-[(2-methylpropan-2-yl)oxycarbonylamino]-5-oxopentanoate
- (S)-4-nitrophenyl 5-amino-2-(tert-butoxycarbonylamino)-5-oxopentanoate
- N-
- N-alpha-t-Butyloxycarbonyl-L-glutamine p-nitrophenyl ester (Boc-L-Gln-ONp)
- CS-0207592
- J-009053
- N2-tert-Butoxycarbonyl-L-glutamine p-nitrophenyl ester; N2-(tert-Butyloxycarbonyl)-L-glutamine p-nitrophenyl ester; N-(tert-Butoxycarbonyl)-L-glutamine p-nitrophenyl ester; L-Boc-glutamine p-nitrophenyl ester
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- MDL： MFCD00065572
- Inchi： 1S/C16H21N3O7/c1-16(2,3)26-15(22)18-12(8-9-13(17)20)14(21)25-11-6-4-10(5-7-11)19(23)24/h4-7,12H,8-9H2,1-3H3,(H2,17,20)(H,18,22)/t12-/m0/s1
- InChI Key： HJMMCTZLXOVMFB-LBPRGKRZSA-N
- SMILES： O(C(N[C@H](C(=O)OC1C=CC(=CC=1)[N+](=O)[O-])CCC(N)=O)=O)C(C)(C)C
Computed Properties
- Exact Mass: 367.13800
- Monoisotopic Mass: 367.138
- Isotope Atom Count: 0
- Hydrogen Bond Donor Count: 2
- Hydrogen Bond Acceptor Count: 7
- Heavy Atom Count: 26
- Rotatable Bond Count: 11
- Complexity: 531
- Covalently-Bonded Unit Count: 1
- Defined Atom Stereocenter Count: 0
- Undefined Atom Stereocenter Count : 1
- Defined Bond Stereocenter Count: 0
- Undefined Bond Stereocenter Count: 0
- Surface Charge: 0
- Tautomer Count: 4
- XLogP3: 1.5
- Topological Polar Surface Area: 151
Experimental Properties
- Color/Form: Not determined
- Density: 1.3±0.1 g/cm3
- Melting Point: Not available
- Boiling Point: 617.5±55.0 °C at 760 mmHg
- Flash Point: 327.2±31.5 °C
- Refractive Index: 1.545
- PSA: 153.54000
- LogP: 3.27340
- Solubility: Not determined
- Vapor Pressure: 0.0±1.8 mmHg at 25°C
Boc-Gln-ONp Security Information
- Signal Word：warning
- Hazard Statement： H303May be harmful if swallowed+H313Skin contact may be harmful+H333Inhalation may be harmful to the body
-
Warning Statement：
P264Thoroughly clean after treatment
P280Wear protective gloves/Wear protective clothing/Wear protective goggles/Wear a protective mask
P305If it enters the eyes
P351Rinse carefully with water for a few minutes
P338Remove the contact lens(If any)And easy to operate,Continue flushing
P337If eye irritation persists
P313Obtain medical advice/care - Hazardous Material transportation number：NONH for all modes of transport
- WGK Germany：3
- Safety Instruction： H303May be harmful if swallowed+H313Skin contact may be harmful+H333Inhalation may be harmful to the body
- FLUKA BRAND F CODES：8
- Storage Condition：2-8°C
Boc-Gln-ONp Pricemore >>
| Related Categories | No. | Product Name | Cas No. | Purity | Specification | Price | update time | Inquiry |
|---|---|---|---|---|---|---|---|---|
| Fluorochem | M03284-5g |
Boc-Gln-ONp |
15387-45-8 | 95% | 5g |
￡20.00 | 2022-02-28 | |
| Fluorochem | M03284-25g |
Boc-Gln-ONp |
15387-45-8 | 95% | 25g |
￡65.00 | 2022-02-28 | |
| Fluorochem | M03284-100g |
Boc-Gln-ONp |
15387-45-8 | 95% | 100g |
￡213.00 | 2022-02-28 | |
| Fluorochem | M03284-250g |
Boc-Gln-ONp |
15387-45-8 | 95% | 250g |
￡452.00 | 2022-02-28 | |
| Chemenu | CM344753-25g |
(4-nitrophenyl) (2S)-5-amino-2-[(2-methylpropan-2-yl)oxycarbonylamino]-5-oxopentanoate |
15387-45-8 | 95%+ | 25g |
$86 | 2022-06-12 | |
| Chemenu | CM344753-100g |
(4-nitrophenyl) (2S)-5-amino-2-[(2-methylpropan-2-yl)oxycarbonylamino]-5-oxopentanoate |
15387-45-8 | 95%+ | 100g |
$258 | 2022-06-12 | |
| SHANG HAI MAI KE LIN SHENG HUA Technology Co., Ltd. | B903596-5g |
BOC-L-GLUTAMINE 4-NITROPHENYL ESTER |
15387-45-8 | ≥95% | 5g |
￥169.20 | 2022-09-02 | |
| SHANG HAI MAI KE LIN SHENG HUA Technology Co., Ltd. | B903596-25g |
BOC-L-GLUTAMINE 4-NITROPHENYL ESTER |
15387-45-8 | ≥95% | 25g |
￥601.20 | 2022-09-02 | |
| TRC | B391795-5g |
Boc-Gln-ONp |
15387-45-8 | 5g |
$ 82.00 | 2023-04-18 | ||
| TRC | B391795-10g |
Boc-Gln-ONp |
15387-45-8 | 10g |
$ 110.00 | 2023-04-18 |
Boc-Gln-ONp Related Literature
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Huading Zhang,Lee R. Moore,Maciej Zborowski,P. Stephen Williams,Shlomo Margel,Jeffrey J. Chalmers Analyst, 2005,130, 514-527
-
Daniel Messmer,Stefan Salentinig,Jakob Heier Nanoscale, 2019,11, 6929-6938
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Shintaro Takata,Yoshihiro Miura Phys. Chem. Chem. Phys., 2014,16, 24784-24789
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Byungho Lim,Jaewon Jin,Jin Yoo,Seung Yong Han,Kyeongyeol Kim,Sungah Kang,Nojin Park,Sang Moon Lee,Hae Jin Kim,Seung Uk Son Chem. Commun., 2014,50, 7723-7726
-
Saeideh Mirfakhraei,Malak Hekmati,Fereshteh Hosseini Eshbala,Hojat Veisi New J. Chem., 2018,42, 1757-1761
Additional information on Boc-Gln-ONp
Comprehensive Overview of Boc-Gln-ONp (CAS No. 15387-45-8): Properties, Applications, and Industry Insights
Boc-Gln-ONp (tert-Butyloxycarbonyl-glutamine-4-nitrophenyl ester), identified by CAS No. 15387-45-8, is a specialized peptide synthesis reagent widely utilized in pharmaceutical and biochemical research. This compound belongs to the family of N-protected amino acid active esters, playing a pivotal role in solid-phase peptide synthesis (SPPS) and other bioconjugation techniques. Its unique molecular structure, featuring a Boc (tert-butoxycarbonyl) protecting group and an ONp (4-nitrophenyl ester) activating group, ensures high reactivity and selectivity in amide bond formation.
In recent years, the demand for Boc-Gln-ONp has surged due to its critical role in developing therapeutic peptides and protein-based drugs. Researchers increasingly focus on optimizing peptide coupling efficiency and minimizing side reactions, making this compound a topic of interest in forums like Peptide Science and Journal of Medicinal Chemistry. Common search queries such as "Boc-Gln-ONp solubility", "Boc-Gln-ONp vs. HOBt esters", and "Boc-Gln-ONp storage conditions" reflect practical concerns in laboratory workflows.
The mechanism of action of Boc-Gln-ONp involves the 4-nitrophenyl ester moiety acting as a leaving group during nucleophilic attack by an amine, facilitating peptide bond formation. This property makes it indispensable for synthesizing glutamine-containing peptides, which are prevalent in immune-modulating therapies and neurodegenerative disease research. Notably, its compatibility with Fmoc/tBu strategies allows seamless integration into modern automated peptide synthesizers.
From a commercial perspective, Boc-Gln-ONp is available in high-purity grades (>98%) to meet GMP standards for preclinical studies. Industry trends show growing adoption in ADC (Antibody-Drug Conjugate) development, where precise linker chemistry is paramount. Discussions on platforms like ResearchGate often highlight its advantages over carbodiimide-based coupling agents in reducing racemization risks.
Stability studies indicate that Boc-Gln-ONp should be stored at -20°C under anhydrous conditions to prevent hydrolysis of the active ester. Analytical techniques such as HPLC and LC-MS are routinely employed to monitor its purity, with typical impurities including hydrolyzed ONp derivatives. These quality control aspects are frequently addressed in ISO-certified peptide synthesis guidelines.
Emerging applications in cryo-EM sample preparation and protein crystallography have further expanded the utility of Boc-Gln-ONp. Its ability to introduce glutamine tags without disrupting protein folding makes it valuable for structural biology studies. Recent publications in Nature Protocols have detailed its use in site-specific labeling of membrane proteins.
Environmental and safety assessments classify Boc-Gln-ONp as requiring standard organic compound handling procedures. While not classified as hazardous under GHS standards, proper PPE (personal protective equipment) including nitrile gloves and safety goggles is recommended during handling. Material Safety Data Sheets (MSDS) emphasize avoidance of prolonged skin contact due to potential nitrophenol exposure.
The synthesis of Boc-Gln-ONp typically involves carbodiimide-mediated coupling between Boc-Gln-OH and 4-nitrophenol, followed by rigorous purification via recrystallization. Process optimization studies published in Organic Process Research & Development have demonstrated yield improvements through controlled temperature gradients and molecular sieve dehydration.
Looking ahead, advancements in continuous flow chemistry may revolutionize production scales for Boc-Gln-ONp and similar amino acid derivatives. The compound's relevance in peptide vaccine development against emerging pathogens positions it as a key material in biopharmaceutical pipelines. Patent analyses show increasing claims incorporating ONp ester chemistry for next-generation drug delivery systems.
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