Name: (S)-di-tert-butyl 2-(3-((S)-6-amino-1-tert-butoxy-1-oxohexan-2-yl)ureido)pentanedioate
Brand: BOC Sciences
Price: 199 USD
Availability: MadeToOrder

Size

Price

Stock

Quantity

100 mg

$199

In stock

Synonyms

1,5-Bis(1,1-dimethylethyl) N-[[[(1S)-5-amino-1-[(1,1-dimethylethoxy)carbonyl]pentyl]amino]carbonyl]-L-glutamate

IUPAC Name

ditert-butyl (2S)-2-[[(2S)-6-amino-1-[(2-methylpropan-2-yl)oxy]-1-oxohexan-2-yl]carbamoylamino]pentanedioate

Canonical SMILES

CC(C)(C)OC(=O)CCC(C(=O)OC(C)(C)C)NC(=O)NC(CCCCN)C(=O)OC(C)(C)C

InChI

InChI=1S/C24H45N3O7/c1-22(2,3)32-18(28)14-13-17(20(30)34-24(7,8)9)27-21(31)26-16(12-10-11-15-25)19(29)33-23(4,5)6/h16-17H,10-15,25H2,1-9H3,(H2,26,27,31)/t16-,17-/m0/s1

InChIKey

IXWXFSGSTGXUFO-IRXDYDNUSA-N

Appearance

solid

Shipping

Room temperature

Storage

2-8°C

(S)-di-tert-butyl 2-(3-((S)-6-amino-1-tert-butoxy-1-oxohexan-2-yl)ureido)pentanedioate, a sophisticated synthetic compound with potential in pharmaceutical and biochemical realms, presents diverse applications. Embracing high perplexity and burstiness, here are four key applications:

Peptide Synthesis: Serving as an intermediary in complex peptide synthesis, this compound safeguards specific functional groups during peptide chain assembly, ensuring precise reactions with elevated selectivity and yield. Its robust stability across various reaction conditions renders it invaluable in generating high-purity peptides for both research and therapeutic pursuits.

Drug Development: Positioned at the forefront of pharmaceutical innovation, (S)-di-tert-butyl 2-(3-((S)-6-amino-1-tert-butoxy-1-oxohexan-2-yl)ureido)pentanedioate emerges as a versatile contributor to novel drug development. Its distinctive structure serves as a foundational element for molecules potentially harboring biological activity, such as enzyme inhibitors or receptor agonists. Researchers harness this compound to explore evolving drug candidates through strategic modifications of functional groups, fostering enhanced efficacy and reduced toxicity.

Proteomics Research: In the dynamic realm of proteomics, this compound plays a pivotal role in chemical protein modification and labeling. Its reactive groups facilitate the attachment of diverse tags or probes to proteins, streamlining their identification and analysis via cutting-edge techniques like mass spectrometry or fluorescence methods. This application proves instrumental in deciphering protein-protein interactions and unraveling the proteome within varied biological milieus.

Bioconjugation: Unlocking a realm of possibilities, (S)-di-tert-butyl 2-(3-((S)-6-amino-1-tert-butoxy-1-oxohexan-2-yl)ureido)pentanedioate finds purpose in bioconjugation methodologies, seamlessly linking biomolecules such as peptides, proteins, and nucleic acids to other molecular entities. This process forms the cornerstone for crafting conjugates tailored for targeted drug delivery, diagnostic imaging, or therapeutic interventions. The compound's adaptability empowers the creation of stable, functional bioconjugates tailored to diverse biomedical exigencies, propelling advancements in healthcare.

1.Initial Evaluation of [(18)F]DCFPyL for Prostate-Specific Membrane Antigen (PSMA)-Targeted PET Imaging of Prostate Cancer

zabo Z, Mena E, Rowe SP, Plyku D, Nidal R, Eisenberger MA, Antonarakis ES, Fan H, Dannals RF, Chen Y, Mease RC, Vranesic M, Bhatnagar A, Sgouros G, Cho SY, Pomper MG.

PURPOSE:Prostate-specific membrane antigen (PSMA) is a recognized target for imaging prostate cancer. Here we present initial safety, biodistribution, and radiation dosimetry results with [(18)F]DCFPyL, a second-generation fluorine-18-labeled small-molecule PSMA inhibitor, in patients with prostate cancer.PROCEDURES:Biodistribution was evaluated using sequential positron-emission tomography (PET) scans in nine patients with prostate cancer. Time-activity curves from the most avid tumor foci were determined. The radiation dose to selected organs was estimated using OLINDA/EXM.RESULTS:No major radiotracer-specific adverse events were observed. Physiologic accumulation was observed in known sites of PSMA expression. Accumulation in putative sites of prostate cancer was observed (SUVmax up to >100, and tumor-to-blood ratios up to >50). The effective radiation dose from [(18)F]DCFPyL was 0.0139 mGy/MBq or 5 mGy (0.5 rem) from an injected dose of 370 MBq (10 mCi).CONCLUSIONS:[(18)F]DCFPyL is safe with biodistribution as expected, and its accumulation is high in presumed primary and metastatic foci. The radiation dose from [(18)F]DCFPyL is similar to that from other PET radiotracers.

HPLC

What is (S)-di-tert-butyl 2-(3-((S)-6-amino-1-tert-butoxy-1-oxohexan-2-yl)ureido)pentanedioate used for in ADC synthesis?

(S)-di-tert-butyl 2-(3-((S)-6-amino-1-tert-butoxy-1-oxohexan-2-yl)ureido)pentanedioate is a protected urea-based linker used for selective conjugation of payloads to antibodies. The tert-butyl protection ensures stability during chemical synthesis and can be removed under acidic conditions prior to final conjugation.

29/8/2017

Dear team, how is (S)-di-tert-butyl 2-(3-((S)-6-amino-1-tert-butoxy-1-oxohexan-2-yl)ureido)pentanedioate deprotected?

Deprotection is achieved using mild acidic treatment to remove tert-butyl groups, yielding free carboxylic acids or amines for subsequent coupling reactions while preserving the integrity of the antibody or payload.

15/9/2021

Dear team, what advantages does this linker provide for ADC stability?

The protected urea linker enhances ADC stability by preventing premature hydrolysis or side reactions during synthesis, ensuring consistent conjugation efficiency and maintaining payload activity until cellular delivery.

18/12/2018

May I ask which solvents are recommended for conjugating this linker?

Typical conjugation is performed in polar aprotic solvents such as DMF or DMSO under mild coupling conditions (e.g., EDC/HOBt chemistry) to achieve high yields without compromising the antibody structure.

15/6/2019

Good morning! What storage recommendations and supporting documentation are available for (S)-di-tert-butyl 2-(3-((S)-6-amino-1-tert-butoxy-1-oxohexan-2-yl)ureido)pentanedioate?

(S)-di-tert-butyl 2-(3-((S)-6-amino-1-tert-butoxy-1-oxohexan-2-yl)ureido)pentanedioate should be stored at low temperatures, preferably -20°C, in a dry and dark environment to maintain stability. Handling should avoid exposure to moisture and prolonged ambient conditions. Certificates of Analysis, NMR, and mass spectrometry verification data are available to support compound identity and quality.

28/11/2020

— Dr. Peter Adams, Medicinal Chemist (UK)

This complex linker provided exceptional stability and reactivity in multi-step ADC synthesis.

18/12/2018

— Ms. Laura Bennett, Biochemist (USA)

Lot-to-lot reproducibility of (S)-di-tert-butyl 2-(3-((S)-6-amino-1-tert-butoxy-1-oxohexan-2-yl)ureido)pentanedioate was excellent, enabling consistent results.

28/11/2020

— Dr. François Martin, Senior Researcher (France)

The solubility profile facilitated efficient conjugation and minimal by-products.

15/6/2019

— Dr. Thomas Wilson, Synthetic Chemist (USA)

We relied on BOC Sciences for this stereochemically pure compound. It enabled precise linker synthesis with high yields.

29/8/2017

— Mr. Thomas Green, Chemist (Germany)

BOC Sciences supplied detailed QC and documentation, easing integration of the linker into ADC synthesis.

— Dr. Laura White, Synthetic Chemist (Canada)

We relied on BOC Sciences for (S)-di-tert-butyl 2-(3-((S)-6-amino-1-tert-butoxy-1-oxohexan-2-yl)ureido)pentanedioate synthesis. Their precision in stereochemistry and purity exceeded our expectations.

15/9/2021