Der α.α‐Dimethyl‐3.5‐dimethoxybenzyloxycarbonyl (Ddz)‐Rest, eine photo‐ und säurelabile Stickstoff‐Schutzgruppe für die Peptidchemie

Birr, Christian; Lochinger, Werner; Stahnke, Gisela; Lang, Peter

doi:10.1002/jlac.19727630118

Cited by 109 publications

(46 citation statements)

References 11 publications

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“…35 -α,α-Dimethyl-3,5-dimethoxybenzyloxycarbonyl (Ddz). 36 Although Ddz is more acid-stable than the Bpoc and the Trt groups, its removal with 1-5% TFA in DCM makes it compatible with t Bu-type side chain protection. , 37 It can also be removed by photolysis at wavelengths above 280 nm, 36 which makes it potentially very useful for SPS library screening procedures.…”

Section: Introductionmentioning

confidence: 99%

Amino Acid-Protecting Groups

2009

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Section: Introductionmentioning

confidence: 99%

Amino Acid-Protecting Groups

2009

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“…On contrast, microflow reactors generally consist of fabricated microchannels usually less than 0.5 mm in thickness that are milled or etched into a planar surface, ranging from bespoken "lab-on-a-chip" designs to highly engineered glass and metal systems (for reviews on microflow photochemistry, see Refs. 11,[17][18][19][20][21][22][23][24][25][26][27][28].…”

Section: Type and Geometry Of The Reactorsmentioning

confidence: 99%

“…17 Historically, rudimentary flow techniques for photochemical applications have been only sparsely reported in the literature, including the use of a spiral glass reactor in vitamin D synthesis (1959), 18 the use of coiled teflon tubing as a gas-phase reactor for the synthesis of methyl chloride (1971) 19 and a procedure for the removal of photolabile protecting groups in peptide synthesis (1972). 20 However, only in early twenty-first century the use of these apparatuses has become intensive. As highlighted by Noël and coworkers, 21 photons are "reactants" with characteristics different from mainstream chemicals and, accordingly, several factors must be taken into account in the design of a flow photochemical reactor, along with the usual mass and energy balances.…”

Section: Introductionmentioning

confidence: 99%

Design Consideration of Continuous-Flow Photoreactors

Protti¹,

Ravelli²,

Fagnoni³

2017

Photochemical Processes in Continuous-Flow Reactors

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“…This third photolabile protecting group was chosen because it is known that photocleavage intermediates do not react with the liberated amine and that photodeprotection is usually quantitative in solution (Scheme 4) (14). A series of I T 0 electrodes were modified with SAMphotolithographic reagent l c and were irradiated at 254 nm over variable periods of time.…”

Section: Irradiation T I M E (Rnin)mentioning

confidence: 99%

Photolithography of self-assembled monolayers: optimization of protecting groups by an electroanalytical method

Jennane¹,

Boutros²,

Giasson³

1996

Can. J. Chem.

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Patterned surfaces presenting a high density of chemically reactive functional groups can be prepared through photolithography of self-assembled monolayers (SAM). In this paper, we report the synthesis and the evaluation of three reagents that can be used in SAM-photolithographic applications. These reagents are made up of a triethoxysilylpropylamine moiety in which the amine is temporarily blocked by photolabile protecting groups: NVOC (0-nitroveratryloxycarbonyl), ONB (0-nitrobenzyl), or DDZ (a,a-dimethyl-3,s-dimethoxybenzyloxycarbonyl). The presence of the triethoxysilyl group allows selfassembled monolayer formation. Release of chemically reactive amino groups is achieved by irradiation of the surface. An electroanalytical method was developed and used to monitor and optimize the three steps of the methodology occurring on surfaces: monolayer formation, photodeprotection, and subsequent functionalization of the released amino groups. Quantitative information on the efficiency of the photodeprotection step was obtained by this method. It was found that the DDZ group is superior to the ONB and NVOC photolabile protecting groups for SAM-photolithographic applications. Percentages of liberated amino groups are generally above 50% with the DDZ group, while they are generally inferior to 25% and 2% for NVOC and ONB, respectively. These differences are attributed to the destruction of some of the released amino groups through a subsequent reaction with the photoproduct, o-nitrosobenzaldehyde for ONB and 3,4-dimethoxy-6-nitrosobenzaldehyde for NVOC, and to partial loss or destruction of the monolayer during prolonged irradiations.Key words: self-assembled monolayers, surface modification, photolithography, photolabile protecting groups, cyclic voltammetry.R6umC : Des motifs prCsentant une haute densite de groupes fonctionnels chimiquement rCactifs peuvent Stre prCparCs sur des surfaces i l'aide de la photolithographie de monocouches auto-assemblCes (MAA). Dans cet article, nous relatons la synthkse et 1'Cvaluation de trois rCactifs pouvant Ctre utilisCs dans des applications de la photolithographie-MAA. Ces rCactifs sont constituCs d'un fragment triCthoxysilylpropylamine dont la fonction amine est temporairement bloquCe par des groupement protecteurs photolabiles : NVOC (0-nitrovCratryloxycarbonyle), ONB (0-nitrobenzyle) ou DDZ (a,a-dimCthy1-3,sdimCthoxybenzyloxycarbonyle). La prCsence du groupe triCthoxysilyle permet la formation de monocouches auto-assemblCes. La libCration des groupements amines chimiquement rCactifs est accomplie par irradiation de la surface. Une mCthode Clectroanalytique a Ct C dCveloppCe et utilisCe pour suivre et optimiser les trois Ctapes de la mCthodologie se produisant i la surface : la formation de la monocouche, la photodCprotection et la fonctionnalisation subskquente des groupes amines libCrCs. De l'information quantitative sur I'efficacitC de 1'Ctape de dkprotection a Ct C obtenue par cette mCthode. I1 a Ct C dCcouvert que le groupe DDZ est supCrieur aux groupes protecteurs...

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Der α.α‐Dimethyl‐3.5‐dimethoxybenzyloxycarbonyl (Ddz)‐Rest, eine photo‐ und säurelabile Stickstoff‐Schutzgruppe für die Peptidchemie

Cited by 109 publications

References 11 publications

Amino Acid-Protecting Groups

Amino Acid-Protecting Groups

Design Consideration of Continuous-Flow Photoreactors

Photolithography of self-assembled monolayers: optimization of protecting groups by an electroanalytical method

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