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Volumn 16, Issue 25, 2010, Pages 7547-7553

A new highly versatile handle for chemistry on a solid support: The pipecolic linker

Author keywords

Amino acids; C terminal modification; Hydrazides; Pipecolic linkers; Solid phase synthesis

Indexed keywords

ACIDIC TREATMENT; AROMATIC AMINES; C TERMINUS; HIGH PURITY; HYDRAZIDES; PEPTIDE CHEMISTRIES; PEPTIDOMIMETICS; POTENTIAL APPLICATIONS; SMALL ORGANIC MOLECULES; SOLID PHASE SYNTHESIS; SOLID SUPPORTS; TERMINAL MODIFICATIONS;

EID: 77954047156     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201000313     Document Type: Article
Times cited : (11)

References (32)
  • 21
    • 77954071071 scopus 로고    scopus 로고
    • The cheap and commercially available cyclohexane-l,4-dicarboxylic acid [CAS 1076-97-7] was used. It was a mixture of cis/trans isomers (77:23 determined by NMR spectroscopy analysis). The stereochemistry of cyclohexane dicarboxylic acid was proven to have no influence on the resin loading (see the Supporting Information, Table S3)
    • The cheap and commercially available cyclohexane-l,4-dicarboxylic acid [CAS 1076-97-7] was used. It was a mixture of cis/trans isomers (77:23 determined by NMR spectroscopy analysis). The stereochemistry of cyclohexane dicarboxylic acid was proven to have no influence on the resin loading (see the Supporting Information, Table S3).
  • 23
    • 77954041604 scopus 로고    scopus 로고
    • Preparation of 7' is described in the Supporting Information
    • Preparation of 7' is described in the Supporting Information.
  • 24
    • 77954048570 scopus 로고    scopus 로고
    • The loading of resin was verified by UV titration of dibenzofulvene- piperidine adduct released upon piperidine treatment of resin 8 Calculations for each loading determination are presented in the Supporting Information
    • The loading of resin was verified by UV titration of dibenzofulvene- piperidine adduct released upon piperidine treatment of resin 8. Calculations for each loading determination are presented in the Supporting Information.
  • 25
    • 77954048906 scopus 로고    scopus 로고
    • -1. The yields of preparation of the linker were calculated on the basis of the maximum theoretical loading
    • -1. The yields of preparation of the linker were calculated on the basis of the maximum theoretical loading.
  • 26
    • 77954067019 scopus 로고    scopus 로고
    • -1) by using convenient two-step solid-phase procedure A for the following experiments of this study
    • -1) by using convenient two-step solid-phase procedure A for the following experiments of this study.
  • 28
    • 77954068012 scopus 로고    scopus 로고
    • As far as SPPS in the reverse N-to-C direction is concerned, special attention should be paid to oxazolone-mediated epimerization In our study, we used a nonepimerisable AIB residue to demonstrate the feasibility of the anchoring strategy and the methyl ester deprotection
    • As far as SPPS in the reverse N-to-C direction is concerned, special attention should be paid to oxazolone-mediated epimerization. In our study, we used a nonepimerisable AIB residue to demonstrate the feasibility of the anchoring strategy and the methyl ester deprotection.
  • 31
    • 77954065521 scopus 로고    scopus 로고
    • 4% of hydrazone formed with acetone was detected by LC/MS
    • 4% of hydrazone formed with acetone was detected by LC/MS.
  • 32
    • 77954072254 scopus 로고    scopus 로고
    • Other curves are presented in the Supporting Information
    • Other curves are presented in the Supporting Information.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.