2019
DOI: 10.1002/psc.3215
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Chemical synthesis of N‐glycosylated insulin‐like androgenic gland factor from the freshwater prawn Macrobrachium rosenbergii

Abstract: Crustacean insulin‐like androgenic gland factor (IAG) of Macrobrachium rosenbergii, a heterodimeric peptide having both four disulfide bonds and an N‐linked glycan, was synthesized by the combination of solid‐phase peptide synthesis and the regioselective disulfide formation reactions. The disulfide isomer of IAG could also be synthesized by the same manner. The conformational analysis of these peptides by circular dichroism (CD) spectral measurement indicated that the disulfide bond arrangement affected the p… Show more

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Cited by 7 publications
(4 citation statements)
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“…The CD spectrum of peptide 5 showed a negative band at 208 nm, which is typical of α‐helix. In addition, the whole spectral pattern of peptide 5 was similar to those of other insulin/relaxin family peptides reported previously 19,39–44 (Figure 4). The helix content of peptide 5 was estimated using BeStSel to be 16.1%.…”
Section: Resultssupporting
confidence: 84%
“…The CD spectrum of peptide 5 showed a negative band at 208 nm, which is typical of α‐helix. In addition, the whole spectral pattern of peptide 5 was similar to those of other insulin/relaxin family peptides reported previously 19,39–44 (Figure 4). The helix content of peptide 5 was estimated using BeStSel to be 16.1%.…”
Section: Resultssupporting
confidence: 84%
“…The downregulation of genes involved in the insulin-like secretion pathway indicates that a PCD cascade effect primed the destruction of the AG and that this led to the inhibition of the production of the insulin-like hormone [ 6 , 35 , 65 , 66 , 67 ]. In fact, this androgenic hormone is normally secreted by the AG in males [ 68 ]. Importantly, this study shows that interactomic analyses permit us to track the activity of a cell-death compound in 5-day-old post-larvae; this will lead to a deeper understanding of its mechanism of action, enabling the knowledge to be applied for medical and ecological biotechnologies.…”
Section: Discussionmentioning
confidence: 99%
“…Furthermore, N‐glycosylation was reported to affect peptide conformation in Maj ‐IAG (Katayama et al . 2014), but not in Mr ‐IAG (Katayama & Nagasawa 2019; Table 1; Fig. 3).…”
Section: Structure Of Iag Gene Chemical Property and Structure Of Iagmentioning
confidence: 95%