TY - JOUR
T1 - Methods for enhancing ring closing metathesis yield in peptides: synthesis of a dicarba human growth hormone fragment
AU - Van Lierop, Bianca
AU - Whelan, Amanda
AU - Andrikopoulos, Sofianos
AU - Mulder, Roger
AU - Jackson, William
AU - Robinson, Andrea
PY - 2010
Y1 - 2010
N2 - Ruthenium-alkylidene catalysed ring closing metathesis (RCM) provides a convenient method for the synthesis of cyclic dicarba peptide analogues. Sequences devoid of turn-inducing residues, however, can often fail to cyclise. A combination of pseudoproline (IPro) insertion and microwave irradiation can be used to enhance RCM yield in these problematic sequences. This strategy is illustrated in the synthesis of a dicarba human growth hormone (hGH) fragment. The structural changes associated with cystine to dicarba replacement were found to change the metabolic profile of the peptide.
AB - Ruthenium-alkylidene catalysed ring closing metathesis (RCM) provides a convenient method for the synthesis of cyclic dicarba peptide analogues. Sequences devoid of turn-inducing residues, however, can often fail to cyclise. A combination of pseudoproline (IPro) insertion and microwave irradiation can be used to enhance RCM yield in these problematic sequences. This strategy is illustrated in the synthesis of a dicarba human growth hormone (hGH) fragment. The structural changes associated with cystine to dicarba replacement were found to change the metabolic profile of the peptide.
UR - http://www.springerlink.com/index/0Q55433366150271.pdf
U2 - 10.1007/s10989-010-9215-y
DO - 10.1007/s10989-010-9215-y
M3 - Article
SN - 1573-3149
VL - 16
SP - 133
EP - 144
JO - International Journal of Peptide Research and Therapeutics
JF - International Journal of Peptide Research and Therapeutics
IS - 3
ER -