4-(Hydroxymethyl)phenoxyacetic Acid Resins

Chemfiles Volume 3 Article 4

These polymer supports show a lability towards trifluoroacetic acid (TFA) similar to Wang resins. Detachment of the final peptide is accomplished using 95% TFA. The amide bond between the “handle” and aminomethyl polystyrene avoids the acid-sensitive benzyl phenyl ether linkage that has been associated with SPPS by-products.(1-2) Supports with the 4-(hydroxymethyl)phenoxyacetic acid handle attached to an aminoethyl base resin (Polystyrene A) are also available. Customary acronyms for the 4- (hydroxymethyl)phenoxyacetic acid handle, which is also called the “Sheppard Linker”, are HMPA, HPA, HMPAA or PAC. Please note that the abbrevation “HMPA” is also frequently used for the highly acid-labile 4-hydroxymethyl-3-methoxyphenoxy acetic acid handle, which is employed in the synthesis of protected peptide acid fragments.

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  1. Sheppard R. C.; Williams B. J. Int. J. Pept. Protein Res. 1982, 20, 454.
  2. Albericio F.; Barany G. Int. J. Pept. Protein Res. 1984, 23, 342.

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