Replacement of hydrogen fluoride in solid phase peptide synthesis by methanesulfonic acid

Nispen, J. W. Van; Polderdijk, J. P.; Janssen, W. P. A.; Greven, H. M.

doi:10.1002/recl.19811001112

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2005

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Cited by 3 publications

References 9 publications

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Synthesis of fragments of arginine vasopressin and oxytocin containing a cystine residue in position 6

Nispen

Hannink

Schoffelmeer

et al. 1984

Recl. Trav. Chim. Pays‐Bas

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The synthesis is described of several fragments of the neurohypophyseal nonapeptide hormones arginine vasopressin and oxytocin. One group of fragments is characterized by the presence of an asymmetrical disulfide (a cystine residue in position 6), a second group consists of dimeric (symmetrical disulfides) fragments. As common intermediates, peptides containing an S‐tritylcysteine residue were synthesized by the fragment condensation approach. Treatment with methoxycarbonylsulfenyl chloride followed by reaction with the free thiol function of cysteine gave the asymmetrical disulfides, while treatment of the S‐tritylcysteine containing peptide with iodine resulted in the corresponding dimers. Peptides with an N‐terminal glutamine residue (position 4) were found to convert spontaneously into the corresponding pyroglutamic acid products.

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Synthesis of fragments of arginine vasopressin and oxytocin containing a cystine residue in position 6

Nispen

Hannink

Schoffelmeer

et al. 1984

Recl. Trav. Chim. Pays‐Bas

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show abstract

Useful Synthetic Preparations

1982

Annual Reports in Organic Synthesis–1981

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Dramatically enhanced N→O acyl migration during the trifluoroacetic acid-based deprotection step in solid phase peptide synthesis

Carpino

Krause²,

Sferdean

et al. 2005

Tetrahedron Letters

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Replacement of hydrogen fluoride in solid phase peptide synthesis by methanesulfonic acid

Abstract: The dangerous I iquid HF, which in addition causes many side-reactions, has successfully been replaced by the easy-to-handle organic acid methanesulfonic acid for the cleavage of smal I peptides from the standard Merrifield resin.

Cited by 3 publications

References 9 publications

Synthesis of fragments of arginine vasopressin and oxytocin containing a cystine residue in position 6

Synthesis of fragments of arginine vasopressin and oxytocin containing a cystine residue in position 6

Useful Synthetic Preparations

Dramatically enhanced N→O acyl migration during the trifluoroacetic acid-based deprotection step in solid phase peptide synthesis

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