S-Acyl isopeptides

Monbaliu JCM, Dive G, Stevens CV, Katritzky AR (2013) Governing parameters of long-range intramolecular S-to-N acyl transfers within (S)-acyl isopeptides. J Chem Theory Comput 9 927-934... 

An application of the method to Alzheimer s A l-42 revealed that the O-acyl isopeptide of Api-42 (in which the Gly -Ser sequence of A 31-42 was isomerized to a P-ester bond) could be synthesized effectively and stored without spontaneous self-assembly (1-3). Intact monomer A -A2 could then be obtained from the isopeptide under physiologic experimental conditions. The water solubility of the TFA salt of the isopeptide was 100-fold higher than that of A 1 2 (0.14mg mL ). Purified isopeptides could be converted quantitatively... 

Taniguchi A, Sohma Y, Kimura M, Okada T, Ikeda K, Hayashi Y, Kimura T, Hirota S, Matsuzaki K, Kiso Y. Click peptide based on the O-acyl isopeptide method control of Afll-42 production from a photo-triggered Af 1 2 analogue. J. Am. Chem. Soc. 2006 128 696-697. 

Sohma Y, Kiso Y. Click peptides -chemical biology-oriented synthesis of Alzheimer s disease-related amyloid (> peptide (Afl) analogues based on the O-acyl isopeptide method . Chem-BioChem. 2006 7 1549-1557. 

Fig. 23 (a) 5- xo-trig S- to W-acyl transfo as commonly encountered in classical NCL and (S)-isopeptide rearrangements (left) and n-exo-aig, S- to IV-acyl transfer in internal Cys NCL and extended isopeptides rearrangements (right), (b) Isomerization of (5)-acyl isopeptides to native peptide analogues if / = 0, = 5... 

Panda SS, Hall CD, Oliferenko AA, Katritzky AR (2014) Traceless chemical ligation from S-, 0-, and A-acyl isopeptides. Acc Chem Res 47 1076-1087... 

The governing parameters for the long-range conversion of (5)-acyl isopeptides (41 X = [CHRCOl OH) to native peptide analogues (42 X = [CHRCO]j OH) via intramolecular S-to-N acyl transfer (Scheme 13) are shown by computational and statistical methods (principal component analysis and cluster analysis) of model... 

Sohma Y, Sasaki M, Hayashi Y, Kimura T, Kiso Y. Design and synthesis of a novel water-soluble A(il-42 isopeptide an efficient strategy for the preparation of Alzheimer s disease-related peptide, Api-42, via O-N intramolecular acyl migration reaction. Tetrahedron Lett. 2004 45 5965-5968. 

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