Boc/Bzl solid phase synthesis of deltorphin II and its analogues without utilization of anhydrous hydrogen fluoride

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Abstract

The toxicity and aggressive nature of hydrogen fluoride have resulted in development of alternative strong Lewis acid-based reagents for final deprotection and cleavage steps in Boc/Bzl peptide synthesis. The acids employed are high-boiling liquids unlike hydrogen fluoride, however most peptides could be quite easily isolated from the cleavage cocktails due to their favorable physico-chemical properties: they are usually precipitated with ether. We found that this simple procedure is not suitable for the isolation of Deltorphin II peptides and its analogues. Therefore we developed alternative isolation methods and successfully purified these peptides. The procedures developed could be utilized in purification of other hydrophibic peptides.

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About the authors

V. N. Azev

Branch of Shemyakin and Ovchinnikov Bioorganic Chemistry Institute RAS

Author for correspondence.
Email: viatcheslav.azev@bibch.ru
Russian Federation, prosp. Nauki 6, Puschino, 142290

L. G. Mustaeva

Branch of Shemyakin and Ovchinnikov Bioorganic Chemistry Institute RAS

Email: viatcheslav.azev@bibch.ru
Russian Federation, prosp. Nauki 6, Puschino, 142290

E. Y. Gorbunova

Branch of Shemyakin and Ovchinnikov Bioorganic Chemistry Institute RAS

Email: viatcheslav.azev@bibch.ru
Russian Federation, prosp. Nauki 6, Puschino, 142290

L. K. Baidakova

Branch of Shemyakin and Ovchinnikov Bioorganic Chemistry Institute RAS

Email: viatcheslav.azev@bibch.ru
Russian Federation, prosp. Nauki 6, Puschino, 142290

A. N. Chulin

Branch of Shemyakin and Ovchinnikov Bioorganic Chemistry Institute RAS

Email: viatcheslav.azev@bibch.ru
Russian Federation, prosp. Nauki 6, Puschino, 142290

L. N. Maslov

Cardiology Research Institute, Tomsk National Research Medical Center RAS

Email: viatcheslav.azev@bibch.ru
Russian Federation, ul. Kievskaya 111-A, Tomsk, 634012

A. V. Mukhomedziyanov

Cardiology Research Institute, Tomsk National Research Medical Center RAS

Email: viatcheslav.azev@bibch.ru
Russian Federation, ul. Kievskaya 111-A, Tomsk, 634012

М. V. Molchanov

Istitute for Theoretical and Experimental Biophysics RAS

Email: viatcheslav.azev@bibch.ru
Russian Federation, ul. Institutskaya 3, Puschino, 142290

A. I. Miroshnikov

Shemyakin and Ovchinnikov Bioorganic Chemistry Institute RAS

Email: viatcheslav.azev@bibch.ru
Russian Federation, ul. Miklukho-Maklaya 16/10, Moscow, 117997

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2. Fig. 1. Chromatograms of stages of the gel filtration process of the mixture of peptide (I) and low-molecular impurities, vertical lines correspond to a time interval of 2 min. (a) – Sephadex G-10 sorbent, no separation upon application of the untreated mixture; (b) – Sephadex G-10, partial separation after distillation of a significant portion of the salts with water vapor before application; (c) – Sephadex LH-20 sorbent, partial separation upon application of the untreated mixture; (d) – Sephadex LH-20 sorbent, almost complete separation after distillation of a significant portion of the salts with water vapor during lyophilization before application.

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