Acylation of nucleophiles

SECTION 8.8. ACYLATION OF NUCLEOPHILIC OXYGEN AND NITROGEN GROUPS... 

Esters of A - hydro x y s u c c i n i in i d c are also used to carry out chemical modification of peptides, proteins, and other biological molecules by acylation of nucleophilic groups in these molecules. For example, detection of estradiol antibodies can be accomplished using... 

One of the most common strategies for preparation of carboxylic acid derivatives is the acylation of nucleophiles of general formula RXH (X = NR, O, S). If the right reaction conditions are chosen and if the product is stable these reactions usually proceed swiftly and in high yield. Some carboxylic acids and nucleophiles, however, do not react smoothly or lead to unexpected results. The following sections cover a selection of representative examples of problematic starting materials. 

Acylation of nucleophilic groups is intended to increase the hydrophobicity of the protein, introduce additional ionizable groups, or contribute to cross-linking ... 

Figure 3, Acylation of nucleophiles by polymer-bound 1-acyl-DMAP chloride.

Acyl-DMAP chloride, acylation of nucleophiles, 242f Acylatlng agents, polyneric, types, 235-238... 

The alkylation of carbon nucleophiles by SN2-type processes is an important transformation in the synthesis of organic compounds. The generation and alkylation of such nucleophiles are described in this chapter. Alkylation and acylation of nucleophilic carbon species by other mechanisms are discussed in Chapter 2. 

The conversion of alcohols to esters by O-acylation and of amines to amides by N-acylation are fundamental organic reactions. These reactions are the reverse of the hydrolytic procedures discussed in the preceding sections. Acylation of nucleophilic carbon is also important, but this topic is deferred until Part B, Chapter 2, where the synthetic aspects of the reaction can be emphasized. 

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