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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 ...
Hantzsch ester refers to an organic compound with the formula HN(MeC=C(CO 2 Et)) 2 CH 2 where Me = methyl (CH 3) and Et = ethyl (C 2 H 5).It is a light yellow solid. The compound is a 1,4-dihydropyridine.
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.
Common uses for this carbodiimide include peptide synthesis, protein crosslinking to nucleic acids, but also in the preparation of immunoconjugates. EDC is often used in combination with N-hydroxysuccinimide (NHS) for the immobilisation of large biomolecules. Recent work has also used EDC to assess the structure state of uracil nucleobases in RNA.
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 ...
Ortho esters are readily hydrolyzed in mild aqueous acid to form esters: . RC(OR ′) 3 + H 2 O → RCO 2 R ′ + 2 R ′ OH. For example, trimethyl orthoformate CH(OCH 3) 3 may be hydrolyzed (under acidic conditions) to methyl formate and methanol; [5] and may be further hydrolyzed (under alkaline conditions) to salts of formic acid and methanol.
The Reformatsky reaction (sometimes transliterated as Reformatskii reaction) is an organic reaction which condenses aldehydes or ketones with α-halo esters using metallic zinc to form β-hydroxy-esters: [1] [2] The Reformatsky reaction. The organozinc reagent, also called a 'Reformatsky enolate', is prepared by treating an alpha-halo ester ...