Base-Mediated One-Pot Synthesis of Aliphatic Diazirines for Photoaffinity Labeling

Wang, Lei; Tachrim, Zetryana Puteri; Kurokawa, Natsumi; Ohashi, Fumina; Sakihama, Yasuko; Hashidoko, Yasuyuki; Hashimoto, Makoto

doi:10.3390/molecules22081389

Cited by 18 publications

(18 citation statements)

References 30 publications

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“…Synthesis of aliphatic diazirines is straightforward and can be readily accomplished in high yields by using the improved methods reported by Wang et al . As mentioned above, the propensity of aliphatic diazirines to undergo rapid β‐H atom transfer leading to an alkene product, as well as photoinitiated rearrangement to give the diazo isomer which undergoes nucleophilic reactions with the solvent, are major limitations of the photochemistry for bimolecular protein modification .…”

Section: Photoactive Reagents That Produce Carbenesmentioning

confidence: 99%

Photochemical Reactions in the Synthesis of Protein–Drug Conjugates

Holland

Gut

Klingler

et al. 2019

Chemistry A European J

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The ability to modify biologically active molecules such as antibodies with drug molecules, fluorophores or radionuclides is crucial in drug discovery and target identification. Classic chemistry used for protein functionalisation relies almost exclusively on thermochemically mediated reactions. Our recent experiments have begun to explore the use of photochemistry to effect rapid and efficient protein functionalisation. This article introduces some of the principles and objectives of using photochemically activated reagents for protein ligation. The concept of simultaneous photoradiosynthesis of radiolabelled antibodies for use in molecular imaging is introduced as a working example. Notably, the goal of producing functionalised proteins in the absence of pre‐association (non‐covalent ligand‐protein binding) introduces requirements that are distinct from the more regular use of photoactive groups in photoaffinity labelling. With this in mind, the chemistry of thirteen different classes of photoactivatable reagents that react through the formation of intermediate carbenes, electrophiles, dienes, or radicals, is assessed.

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Section: Photoactive Reagents That Produce Carbenesmentioning

confidence: 99%

Photochemical Reactions in the Synthesis of Protein–Drug Conjugates

Holland

Gut

Klingler

et al. 2019

Chemistry A European J

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“…The dehydrogenation of the NH-NH bond in aliphatic diaziridine is a crucial transformation for generating the N=N double bond that acts as the main skeleton of aliphatic 3H-diazirine [57]. In the conventional method, different oxidants, including silver oxide or iodine in the presence of triethylamine, are introduced in order to transform diaziridines into 3H-diazirine following the removal of the ammonia [14,[58][59][60]. Diaziridines are basic and form salts, and in several cases, the pure form of diaziridines can be difficult to isolate [59].…”

Section: Conventional Methods For Recent Usesmentioning

confidence: 99%

“…The alternative method for dehydrogenation of hydroazobenzene, combining the least expensive bulk chemicals of liquid NH 3 as a solvent and the readily available tBuOK system as a base, could be applied for the dehydrogenation of diaziridine [57]. Following this improvement, the use of base that can be easily handled and stored, as well as being highly available, such as KOH could enable gram-scale production [58]. Table 2 (Entries 1-8) shows the representative in situ formation of diaziridine 47a-h for the synthesis of 3H-diazirine 48.…”

Section: Conventional Methods For Recent Usesmentioning

confidence: 99%

New Trends in Diaziridine Formation and Transformation (a Review)

et al. 2021

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This review focuses on diaziridine, a high strained three-membered heterocycle with two nitrogen atoms that plays an important role as one of the most important precursors of diazirine photoaffinity probes, as well as their formation and transformation. Recent research trends can be grouped into three categories, based on whether they have examined non-substituted, N-monosubstituted, or N,N-disubstituted diaziridines. The discussion expands on the conventional methods for recent applications, the current spread of studies, and the unconventional synthesis approaches arising over the last decade of publications.

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“…In particular, we have aimed at a set of functionalized spirocyclic compounds containing diazirine fragment 6a–l (Figure ). It should be noted that of these building blocks, only Boc‐protected derivatives of amines 6c and 6f , and carboxylic acid 6h were reported in the literature , , …”

Section: Introductionmentioning

confidence: 99%