Total synthesis of human glicentin

Mochizuki, Tohru; Ohshima, Keiichi; Takatuka, Naoki; Sato, Keigo; Kakuyama, Hiroyoshi; Iguchi, Kazuaki; Yanaihara, Noboru

doi:10.1007/978-94-011-1474-5_47

Cited by 1 publication

(8 citation statements)

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“…To evaluate the importance of the C-terminal moiety, two C-terminal fragments active on gastric acid secretion, namely OXM(19-37) and OXM (30)(31)(32)(33)(34)(35)(36)(37), were also tested. OXM (19)(20)(21)(22)(23)(24)(25)(26)(27)(28)(29)(30)(31)(32)(33)(34)(35)(36)(37) showed the same efficacy as the mother molecule (14.9 ± 1.1% decrease in cell length at 10 -7 M, n = 9) but was 14.5-fold less potent than GLIC and as potent as OXM (Fig. 3) (EC 50 = 72 pM).…”

Section: Distribution Of Cell Lengthmentioning

confidence: 97%

“…Synthetic human glicentin was synthesized as previously described [28]. [Nle 27 ]-Oxyntomodulin was synthesized according to a procedure published elsewhere [1].…”

Section: Peptidesmentioning

confidence: 99%

“…OXM (19)(20)(21)(22)(23)(24)(25)(26)(27)(28)(29)(30)(31)(32)(33)(34)(35)(36)(37) and OXM (30)(31)(32)(33)(34)(35)(36)(37) were synthesized in our laboratory by the solid-phase method using chloromethylated resin and the Boc-HF strategy. The coupling reactions were carried out manually with the use of benzotriazolyl-oxy tris dimethyl aminophosphonium hexafluorophosphate (BOP) [22].…”

Section: Peptidesmentioning

confidence: 99%

“…GLIC, the 69-amino-acid peptide corresponding to proglucagon 1-69, contains the whole OXM sequence and an N-terminal 32-amino-acid extension. Replicas of the human peptide were recently obtained using a recombinant [17] and a chemical synthesis approach [28]. OXM, the 37-amino-acid peptide corresponding to proglucagon 33-69, contains the glucagon sequence and a C-terminal octapeptide.…”

Section: Introductionmentioning

confidence: 99%

“…This work has demonstrated a specific myogenic effect of these hormones. The structure-activity relationship was investigated using GLIC, OXM and the two Cterminal fragments, OXM (19)(20)(21)(22)(23)(24)(25)(26)(27)(28)(29)(30)(31)(32)(33)(34)(35)(36)(37) and OXM(30-37).…”

Section: Introductionmentioning

confidence: 99%

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Effect of glicentin, oxyntomodulin and related peptides on isolated gastric smooth muscle cells

Rodier

Magous

Mochizuki

et al. 1997

Pfl�gers Archiv European Journal of Physiology

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Glicentin (proglucagon 1-69 GLIC) and oxyntomodulin (proglucagon 33-69 or OXM) are two peptide hormones that are co-released from ileum and large intestine during digestion. They modulate in vivo gastric acid secretion and the gastro-pyloro-duodenal activity. The specificity of their effects is linked to the presence of their C-terminal octapepide. As yet, no isolated target cell that responds specifically to this family of peptides has been described. The present report describes the in vitro effect of human synthetic GLIC, OXM and octapeptide-bearing fragments on smooth muscle cells isolated from the rabbit antrum. GLIC or OXM decreased the mean length of the cells by: 13.9 +/- 0.8% and 15.5 +/- 0.9%, respectively - GLIC being 16 times more potent than OXM (respective EC50 values: 5 and 83 pM). The C-terminal fragments OXM(19-37) and OXM(30-37) were as efficient as GLIC or OXM. Their potencies were OXM = OXM(19-37)>>OXM(30-37). Glucagon, which corresponds to OXM without the C-terminal octapeptide, or glucagon-like peptide-1 (7-36 amide) did not have any effect. The response to OXM was not influenced by antagonists to muscarinic, cholecystokinin or substance P receptors. In conclusion, our studies demonstrate for the first time an isolated target cell that responds specifically to GLIC, OXM and other octapeptide-bearing peptides.

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Section: Distribution Of Cell Lengthmentioning

confidence: 97%

“…Synthetic human glicentin was synthesized as previously described [28]. [Nle 27 ]-Oxyntomodulin was synthesized according to a procedure published elsewhere [1].…”

Section: Peptidesmentioning

confidence: 99%