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Literature DB >> 19725529

Solid-phase synthesis of peptidyl thioacids employing a 9-fluorenylmethyl thioester-based linker in conjunction with Boc chemistry.

Abstract

A method for the synthesis of peptidyl thioacids is described on the basis of the use of the N-[9-(thiomethyl)-9H-fluoren-2-yl]succinamic acid and cross-linked aminomethyl polystyrene resin. The method employs standard Boc chemistry SPPS techniques in conjunction with 9-fluorenylmethyloxycarbonyl protection of side-chain alcohols and amines and 9-fluorenylmethyl protection of side-chain acids and thiols. Cleavage from the resin is accomplished with piperidine, which also serves to remove the side-chain protection and avoids the HF conditions usually associated with the resin cleavage stage of Boc chemistry SPPS. The so-obtained thioacids are converted to simple thioesters in high yield by standard alkylation according to well-established methods.

Entities: CellLine Chemical Gene Species

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Year: 2009 PMID： 19725529 PMCID： PMC2778002 DOI： 10.1021/jo901218g

Source DB: PubMed Journal: J Org Chem ISSN： 0022-3263 Impact factor: 4.354

39 in total

1. Protein synthesis by native chemical ligation: expanded scope by using straightforward methodology.

Authors: T M Hackeng; J H Griffin; P E Dawson
Journal: Proc Natl Acad Sci U S A Date: 1999-08-31 Impact factor: 11.205

2. Fmoc-Compatible Solid-Phase Peptide Synthesis of Long C-Terminal Peptide Thioesters The authors are grateful to the ETH-Zürich and Novartis Pharma AG for support of this work. Fmoc=9-fluorenylmethoxycarbonyl.

Authors: Axel Sewing; Donald Hilvert
Journal: Angew Chem Int Ed Engl Date: 2001-09-17 Impact factor: 15.336

Review 3. Synthesis of native proteins by chemical ligation.

Authors: P E Dawson; S B Kent
Journal: Annu Rev Biochem Date: 2000 Impact factor: 23.643

4. Toward fully synthetic glycoproteins by ultimately convergent routes: a solution to a long-standing problem.

Authors: J David Warren; Justin S Miller; Stacy J Keding; Samuel J Danishefsky
Journal: J Am Chem Soc Date: 2004-06-02 Impact factor: 15.419

5. In situ neutralization in Boc-chemistry solid phase peptide synthesis. Rapid, high yield assembly of difficult sequences.

Authors: M Schnölzer; P Alewood; A Jones; D Alewood; S B Kent
Journal: Int J Pept Protein Res Date: 1992 Sep-Oct

6. Preparation of 'side-chain-to-side-chain' cyclic peptides by Allyl and Alloc strategy: potential for library synthesis.

Authors: P Grieco; P M Gitu; V J Hruby
Journal: J Pept Res Date: 2001-03

7. Backbone Amide Linker (BAL) Strategy for N(alpha)()-9-Fluorenylmethoxycarbonyl (Fmoc) Solid-Phase Synthesis of Unprotected Peptide p-Nitroanilides and Thioesters(1).

Authors: Jordi Alsina; T. Scott Yokum; Fernando Albericio; George Barany
Journal: J Org Chem Date: 1999-11-26 Impact factor: 4.354

2. Dihydro-3-(triphenylphosphoranylidene)-2,5-thiophendione: A Convenient Synthon for the Preparation of Substituted 1,4-Thiazepin-5-ones and Piperidinones via the Intermediacy of Thioacids.

Authors: David Crich; Md Yeajur Rahaman
Journal: Tetrahedron Date: 2010-08-14 Impact factor: 2.457

2 in total

Solid-phase synthesis of peptidyl thioacids employing a 9-fluorenylmethyl thioester-based linker in conjunction with Boc chemistry.

1. Protein synthesis by native chemical ligation: expanded scope by using straightforward methodology.

2. Fmoc-Compatible Solid-Phase Peptide Synthesis of Long C-Terminal Peptide Thioesters The authors are grateful to the ETH-Zürich and Novartis Pharma AG for support of this work. Fmoc=9-fluorenylmethoxycarbonyl.

Review 3. Synthesis of native proteins by chemical ligation.

4. Toward fully synthetic glycoproteins by ultimately convergent routes: a solution to a long-standing problem.

5. In situ neutralization in Boc-chemistry solid phase peptide synthesis. Rapid, high yield assembly of difficult sequences.

6. Preparation of 'side-chain-to-side-chain' cyclic peptides by Allyl and Alloc strategy: potential for library synthesis.

7. Backbone Amide Linker (BAL) Strategy for N(alpha)()-9-Fluorenylmethoxycarbonyl (Fmoc) Solid-Phase Synthesis of Unprotected Peptide p-Nitroanilides and Thioesters(1).

8. Fmoc solid-phase synthesis of peptide thioesters by masking as trithioortho esters.

9. Ns strategies: a highly versatile synthetic method for amines.

10. The reaction of thio acids with azides: a new mechanism and new synthetic applications.

1. Convergent synthesis of aminomethylene peptidomimetics.

2. Dihydro-3-(triphenylphosphoranylidene)-2,5-thiophendione: A Convenient Synthon for the Preparation of Substituted 1,4-Thiazepin-5-ones and Piperidinones via the Intermediacy of Thioacids.