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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]
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 ...
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 ...
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.
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.
In micorarray experiments DNA or RNA is labeled with either Cy3 or Cy5 that has been synthesized to carry an N-hydroxysuccinimidyl ester (NHS-ester) reactive group. Since NHS-esters react readily only with aliphatic amine groups, which nucleic acids lack, nucleotides have to be modified with aminoallyl groups. This is done through incorporating ...
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 ...
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.