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It finds its application as a reagent for protection of carboxyl termini of peptides as 4-picolyl esters, providing a polar 'handle' which aids in separation and purification of the peptide. The group can be introduced in the presence of a base, e.g. tetramethylguanidine, is stable to acid-catalyzed removal of Cbz protecting group and can be removed by base, Na in liquid ammonia or catalytic hydrogenolysis. It is also applied in conjunction with Amberlyst®15 resin in peptide synthesis. It is an important raw material and intermediate used in organic synthesis, pharmaceuticals and agrochemicals.
Hongwei Hou, et al. A novel coordination polymer [Co(NCS)2(bpms)2]n (bpms=1,2-bis(4-pyridylmethyl)disulfenyl): synthesis, crystal structure and third-order nonlinear optical properties.
Ping Zhou, et al.TA new efficient synthesis of 3-(4-pyridinyl)methylindoles.
Reagent for protection of carboxyl termini of peptides as 4-picolyl esters, providing a polar 'handle' which aids in separation and purification of the peptide. The group can be introduced in the presence of a base, e.g. tetramethylguanidine, is stable to acid-catalyzed removal of Cbz protecting group and can be removed by base, Na in liquid ammonia or catalytic hydrogenolysis: J. Chem. Soc. (C), 1911 (1969); 46, 50 (1971). For use in conjunction with Amberlyst®15 resin in peptide synthesis, see: J. Chem. Soc., Chem. Commun., 1057 (1971). For an alternative means of introduction, see 4-Pyridinemethanol, A14698.
As its free base, has been used for the protection of OH groups as 4-picolyl derivatives, relatively stable to acid (HF, TFA) but selectively cleaved by electrolytic reduction: J. Chem. Soc., Chem. Commun., 1123 (1972); Acta Chem. Scand. B, B37, 475 (1983); J. Chem. Res. (Synop.), 22 (1977). For use in the protection of the hydroxyl-substituted amino acids serine and threonine as their 4-picolyl ethers, see: J. Org. Chem., 53, 5386 (1988). In this case the group was cleaved by hydrogenolysis in AcOH. See also Appendix 6.
Hazard Statements: H302-H314
Harmful if swallowed. Causes severe skin burns and eye damage.
Precautionary Statements: P260-P264b-P270-P280-P303+P361+P353-P304+P340-P305+P351+P338-P310-P330-P331-P363-P501c
Do not breathe dust/fume/gas/mist/vapours/spray. Wash face, hands and any exposed skin thoroughly after handling Do not eat, drink or smoke when using this product. Wear protective gloves/protective clothing/eye protection/face protection. IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Immediately call a POISON CENTER or doctor/physician. Rinse mouth. Do NOT induce vomiting. Wash contaminated clothing before reuse. Dispose of contents/ container to an approved waste disposal plant