Anda di halaman 1dari 2
Description Kaiser oxime resin Synonyms p -Nitrobenzophenone oxime resin Applications Oxime resin was originally introduced to

Description

Kaiser oxime resin

Synonyms

p-Nitrobenzophenone oxime resin

Applications

Oxime resin was originally introduced to allow the synthesis of fully protected peptide fragments using Boc chemistry. Traditionally, peptides produced using resins designed for Boc chemistry have benzyl-based side chain protection which is removed at the same time as final cleavage. The ability to cleave peptide fragments using hydrazinolysis with the side chain protecting groups intact allows for the production of peptide hydrazides. These can then be used to generate azides for fragment assembly.

Alternative cleavage techniques with other nucleophiles allow generation of esters as well as free acids, and other peptide analogs such as thioacids, hydroxamates and glycopeptides.

Oxime resins have also proved useful in the synthesis of cyclic peptides.

Note: Repeated exposure of the resin to trifluoroacetic acid (as used in Boc removal) can result in slight losses through premature cleavage.

Description Kaiser oxime resin Synonyms p -Nitrobenzophenone oxime resin Applications Oxime resin was originally introduced to
Description Kaiser oxime resin Synonyms p -Nitrobenzophenone oxime resin Applications Oxime resin was originally introduced to

References

DeGrado, W F & Kaiser, E T (1980), J Org Chem, 45, 1295 DeGrado, W F & Kaiser, E T (1982), J Org Chem, 47, 3258 Lee, Y-S & You, W-S (1985), Bull Korean Chem Soc, 6, 380 Park, D-H et al (1988), Bull Korean Chem Soc, 9, 394 Jarrett, J T & Lansbury Jr, P T (1990), Tetrahedron Lett, 31,

4561

Ösapay, G et al (1990), Tetrahedron Lett, 31, 6121

Schwabacher, A W & Maynard, T L (1993), Tetrahedron Lett, 34, 1269

Nishino, N et al (1992), J Chem Soc, Chem Commun, 180 Bouvier, M & Taylor, J W (1992), J Med Chem, 35, 1145 Park, D-H & Lee, Y-S (1993), Bull Korean Chem Soc, 14,

419

Mihara, H et al (1993), Int J Peptide Protein Res, 41, 405 Ösapay, G & Goodman, M (1993), J Chem Soc, Chem Commun, 1599 Bauman, A C et al (1993), Tetrahedron Lett, 34, 7019 Kapurniotu, A & Taylor, J W (1993), Tetrahedron Lett, 34,

7031

Voyer, N et al (1994), Tetrahedron Lett, 35, 355 Ösapay, G et al (1995), Int J Peptide Protein Res, 46, 290 Mihara, H et al (1995), Tetrahedron Lett, 36, 4837 Lumma Jr, W C et al (1998), J Med Chem, 41, 1011

Products Information

Microporous

PL-Oxime Resin

0.6mmol/g 75-150µm (100-200 mesh)

Description Kaiser oxime resin Synonyms p -Nitrobenzophenone oxime resin Applications Oxime resin was originally introduced to

Description

Kaiser oxime resin

Synonyms

p-Nitrobenzophenone oxime resin

Applications

Oxime resin was originally introduced to allow the synthesis of fully protected peptide fragments using Boc chemistry. Many compound libraries are generated using amino acids as a building block, and the use of PL-Oxime Resin can add to the diversity by enabling a variety of transformations to be performed during the cleavage reaction.

Acids can be converted into esters, hydrazides, thioacids and hydroxamates for example.

Description Kaiser oxime resin Synonyms p -Nitrobenzophenone oxime resin Applications Oxime resin was originally introduced to

References

DeGrado, W F & Kaiser, E T (1980), J Org Chem, 45, 1295 DeGrado, W F & Kaiser, E T (1982), J Org Chem, 47, 3258 Kaiser, E T et al (1989), Science, 243, 187 Ösapay, G & Taylor, J W (1990), J Am Chem Soc, 112,

6046

Jarrett, J T & Lansbury Jr, P T (1990), Tetrahedron Lett, 31,

4561

Ösapay, G et al (1990), Tetrahedron Lett, 31, 6121 Nishino, N et al (1992), J Chem Soc, Chem Commun, 180 Bouvier, M & Taylor, J W (1992), J Med Chem, 35, 1145 Hendrix, J C et al (1992), J Org Chem, 57, 3414 Ösapay, G & Goodman, M (1993), J Chem Soc, Chem Commun, 1599 Schwabacher, A W & Maynard, T L (1993), Tetrahedron Lett, 34, 1269 Nishino, N et al (1993), Tetrahedron Lett, 34, 1295

Bauman, A C et al (1993), Tetrahedron Lett, 34, 7019

Kapurniotu, A & Taylor, J W (1993), Tetrahedron Lett, 34,

7031

Mihara, H et al (1993), J Org Chem, 58, 2209 Mihara, H et al (1993), Int J Peptide Protein Res, 41, 405 Voyer, N et al (1994), Tetrahedron Lett, 35, 355 Ösapay, G et al (1995), Int J Peptide Protein Res, 46, 290 Mihara, H et al (1995), Tetrahedron Lett, 36, 4837 Lumma Jr, W C et al (1998), J Med Chem, 41, 1011 Golebiowski, A & Klopfenstein, S (1998), Tetrahedron Lett, 39, 3397 Lepore, S D & Wiley, M R (1999), J Org Chem, 64, 4547 Lepore, S D & Wiley, M R (2000), J Org Chem, 65, 2924 Dolence, E K et al (2000), J Comb Chem, 2, 522 Tremblay, M et al (2002), J Comb Chem, 4, 429

Products Information

Microporous

PL-Oxime Resin

0.6mmol/g 150-300µm (50-100 mesh)