ADCC-linker

ADCC linker (stable to acidic and basic conditions... 

Other cleavage procedures listed in Section 5.3 include use of a Grignard reagent to generate alcohols, the synthesis of amines by cleavage with hydrazine (ADCC linker), and the generation of tertiary amines by Hoffmann-elimination (acrylic acid linker). 

The 4-acetyl-3,5-dioxo-l-methylcyclohexane carboxylic acid (ADCC) linker 2n [128] was developed to provide a support for anchoring primary amines via a preformed handle method. The anchor is stable toward acids and bases including piperidine and l,8-diazabicyclo[5.4.0]undec-7-ene (DBU) and is thus compatible with Fmoc chemistry. The amine can be released by rapid hydrazinolysis on treatment with 2% hydrazine in DMF. A formamidine linker 2o has been obtained from Merrifield resin by reaction with the appropriate phenol. Secondary amines can be anchored to the support by an amidine exchange reaction and after further transformations cleaved by treatment with hydrazine [129]. 

Typical nucleophilically cleavable linkers are the REM resin linker 86 [75] (polymer-bound benzyl acrylate regenerated Michael acceptor) and the Dde group 87 (ADCC (4-Acetyl-3,5-dioxo-l-methylcyclohexane carboxylic acid) anchor) [76], which are linkers for tertiary and primary amines, respectively (Figure 6.1.7). 

AA, amino acid AC, acid-cleavable linker [4-(hydroxymethyl)-3-methoxy-phenoxy]acetic acid ADCC, 4-acetyl-3,5-dioxo-l-methylcyclohexane carboxylic acid AMEBA, acid-sensitive methoxybenzyl resin ANP, 3-amino(2-nitrophenyl)propionyl BAL, backbone amide linker 9-BBN,... 

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