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N-Hydroxysuccinimide (NHS) is an organic compound with the formula (CH 2 CO) 2 NOH. It is a white solid that is used as a reagent for preparing active esters in peptide synthesis. It can be synthesized by heating succinic anhydride with hydroxylamine or hydroxylamine hydrochloride. [2]
Disuccinimidyl suberate (DSS) is the non-water-soluble analog of BS3. DSS and BS3 express the same crosslinking ability toward primary amines. [ 16 ] The major structural difference between these two molecules is that DSS does not contain the sulfonate substituents at either end of the molecule, and it is this difference that is responsible for ...
Water purification combines a number of methods to produce potable or drinking water. Downstream processing refers to purification of chemicals, pharmaceuticals and food ingredients produced by fermentation or synthesized by plant and animal tissues, for example antibiotics, citric acid, vitamin E, and insulin.
Active esters are often used in peptide synthesis, e.g., N-hydroxysuccinimide, hydroxybenzotriazole. [1] Active esters of acrylic acid are precursors to polymers with reactive side chains. [4] The concept of active esters extends to esters of phosphoric and sulfuric acids. One such case is dimethylsulfate, a strong methylating agent.
An example of an ester formation is the substitution reaction between a carboxylic acid (R−C(=O)−OH) and an alcohol (R'OH), forming an ester (R−C(=O)−O−R'), where R and R′ are organyl groups, or H in the case of esters of formic acid.
In protein synthesis (such as Fmoc solid-state synthesizers), the N-terminus is often used as the attachment site on which the amino acid monomers are added. To enhance the electrophilicity of carboxylate group, the negatively charged oxygen must first be "activated" into a better leaving group. DCC is used for this purpose.
The ester linkage is formed between the N-hydroxyphthalimide and a carboxylic acid by elimination of water, the coupling achieved with N,N′-dicyclohexylcarbodiimide (DCC). For peptide synthesis, the N-terminus of the growing peptide is protected with tert-butyloxycarbonyl while its C-terminus (Z–NH–CH(R)–COOH) is coupled to N ...
HATU was first reported by Louis A. Carpino in 1993 as an efficient means of preparing active esters derived from 1-hydroxy-7-azabenzotriazole (HOAt). [2] HATU is commonly prepared from HOAt and TCFH under basic conditions [3] and can exist as either the uronium salt (O-form) or the less reactive iminium salt (N-form).