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Amino acid and peptide conjugates and conjugation process

一种氨基酸、氨基保护基的技术，应用在制造用于其的药物,氨基酸及肽共轭物的化合物领域，能够解决疫苗制备复杂等问题

Inactive Publication Date: 2018-11-23
AUCKLAND UNISERVICES LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] Several self-adjuvanted vaccines have been developed, but preparation of such vaccines can be complicated

Method used

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  • Amino acid and peptide conjugates and conjugation process
  • Amino acid and peptide conjugates and conjugation process
  • Amino acid and peptide conjugates and conjugation process

Examples

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preparation example Construction

[0732] The preparation of such compounds may involve the protection and deprotection of a variety of different chemical groups. The need for protection and deprotection, as well as the selection of appropriate protecting groups, can be readily determined by those skilled in the art. Protecting groups and methods for protection and deprotection are well known in the art (see, e.g., T.W. Greene and P.G.M. Wuts, Protective Groups in Organic Synthesis, 3 rd Ed., Wiley & Sons, Inc., New York (1999)).

[0733] As shown in Scheme A1 and described below, the compound of formula (IF) is a compound of formula (I) wherein w is 1, v is 0 and m is 2 to 6, preferably 2, which can be obtained by involving the ring Prepared by conjugation of an oxide to a conjugation partner containing an amino acid.

[0734] Scheme A1: Preparation of compounds of formula (IF) via conjugation to epoxides.

[0735]

[0736] The present invention provides a method for the preparation of formula (XV), com...

example 1

[1067] This example describes the preparation of peptide conjugate 3 of the invention via a thiolene reaction.

[1068] 1.1 General Details and Methods

[1069] Protected amino acids and couplers were purchased from GL-Biochem (Shanghai). The resin used in the immobilization synthesis was a tentagel resin derived with a linker and the first (C-terminal) residue of the peptide sequence from Rapp Polymere GmbH (Tübingen), and other solvents and reagents were obtained from Sigma (St. Lewis) and Novabiochem.

[1070] Peptide synthesis described below was performed on a Tribute peptide synthesizer (Protein Technologies International, Tucson, AZ) using standard repetitive Fmoc solid-phase peptide synthesis techniques.

[1071] A typical deprotection and coupling cycle on a 0.1 mmol scale requires two treatments with 20% piperidine in DMF (4 mL x 5 min) followed by washing the resin with DMF to remove Fmoc protection from the resin-bound amino acids base. In a separate container,...

example 2

[1103] This case study:

[1104] 1. Mice of the present invention and people's TLR2 agonism, in two kinds of variation---homoPam2Cys (NH 2 )-SKKKK and homoPam2Cys(NHAc)-SKKKK - compared to the well-known TLR2 agonists PamlCys-SKKK, Pam2Cys-SKKKK and Pam3Cys-SKKKK. In all cases, agonists were prepared in-house and isolated via semi-preparative HPLC as described for Example 1, except that Pam3Cys-SKKK was purchased from InvivoGen. In addition, the retention of TLR2 agonism when conjugated to short peptide epitopes was assessed relative to Pam3Cys-SKKKK. In this example, homoPam2Cys(NHAc)-SKKK-'NLV' was generated as described for Invention 3 (separated by semi-preparative HPLC as described in Example 1), except that the conjugate peptide sequence was NLVPMVATVK(Ac) . A matching Pam2Cys-SKKKK-NLVPMVATVK(Ac) was also prepared.

[1105]2. Release and presentation of conjugated short synthetic peptides and long synthetic peptides to homologous CD8+ T cell clones. In this example...

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Abstract

The invention relates to amino acid and peptide conjugates, methods for making amino acid and peptide conjugates, conjugates produced by the methods, and pharmaceutical compositions comprising the conjugates. Methods of eliciting immune responses in a subject and methods of vaccinating a subject, uses of the conjugates for the same, and uses of the conjugates in the manufacture of medicaments forthe same are also contemplated.

Description

technical field [0001] The present invention relates to amino acid and peptide conjugates, methods for preparing amino acid and peptide conjugates, conjugates produced by said methods, pharmaceutical compositions comprising said conjugates, methods for eliciting an immune response in a subject Methods and methods of vaccinating subjects, uses of said conjugates therefor and uses of said conjugates in the manufacture of medicaments therefor. The invention also relates to methods of preparing compounds useful in the synthesis of the amino acid and peptide conjugates of the invention and to such compounds. Background technique [0002] Synthetic peptide vaccines generally contain synthetic copies of immunogenic portions of protein antigens. This approach to vaccine development has many advantages, including ease of synthesis, avoidance of potentially toxic biological by-products, and ease of characterization. [0003] A key problem in developing peptide vaccines is that pepti...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C229/02C07C227/16C07C321/12C07K14/00C07K14/435C07K1/02
CPCA61P35/00A61K39/001104A61K39/02A61K39/12A61K39/39C07C323/59C07K7/00A61K2121/00A61K39/001188C07K7/02C07K14/70539A61K47/543A61K2039/6018C12N2710/16234A61K2039/627C07K7/08C07K14/001C07K19/00C07K1/04C07K1/063C07K1/10A61K39/385A61K2039/55516A61K2039/58
Inventor 玛格丽特·安妮·布林布尔杰弗里·马丁·威廉斯彼得·罗德里克·邓巴丹尼尔·弗登
Owner AUCKLAND UNISERVICES LTD
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