Synthesis of ketones and aldehydes via reactions of Weinreb-type amides on solid support

Dinh, Tam Q.; Armstrong, Robert W.

doi:10.1016/0040-4039(95)02400-x

Cited by 68 publications

(29 citation statements)

References 5 publications

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“…We first approached the synthesis of WK 18 LLnV-vinyl ester (ve), by releasing the fully protected WK 18 LLnV-aldehyde from the Weinreb amide resin with LAH, followed by its direct conversion to the vinyl ester using a Horner-Wadsworth-Emmons reaction (19,(24)(25)(26). This strategy was successful, but only afforded 1% yields of the desired WK 18 LLnV-ve and proved difficult to optimize.…”

Section: Resultsmentioning

confidence: 99%

A Novel Class of Intrinsic Proteasome Inhibitory Gene Transfer Peptides

Martin

Rice

2007

Bioconjugate Chem.

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Proteasomes are multisubunit enzymes responsible for the degradation of many cytosolic proteins. The inhibition of the proteasome has been the subject of intense interest in the development of drug therapies. We have previously demonstrated that simultaneous administration of a tripeptide aldehyde proteasome inhibitor (MG115 or MG132) with a peptide (Cys-Trp-Lys 18 ) DNA condensate boosted gene expression by 30-fold in cell culture. In the present study, we have developed a convergent synthesis to allow the incorporation of a proteasome inhibitor tripeptide into the C-terminal end of a gene delivery peptide. The resulting peptides formed DNA condensates that mediated a 100-fold enhancement in gene expression over a control peptide lacking all or part of the tripeptide inhibitor. Gene transfer peptides possessing intrinsic proteasome inhibitors were also found to be non-toxic to cells in culture. These results suggest that intrinsic proteasome inhibition may also be used to boost the efficiency of peptide mediated nonviral gene delivery systems in vivo.

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Section: Resultsmentioning

confidence: 99%

A Novel Class of Intrinsic Proteasome Inhibitory Gene Transfer Peptides

Martin

Rice

2007

Bioconjugate Chem.

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“…Further, several N-protected di and tri-peptide derived Weinreb amides 4a-g were also synthesized (Scheme 2) and have been obtained in good yields ( Table 3). The structural assignment of the Weinreb amides 2 and 4 was made on the basis of 1 H, 13 C NMR, and mass spectral data. Fig.…”

Section: T R a C Tmentioning

confidence: 99%

“…10 Classically, these derivatives have been synthesized by the treatment of N,O-dimethylhydroxylamine with an activated carboxylic group. Several peptide coupling reagents have been employed in this transformation which include BOP, 11 DCC, 12 DCC/HOBt, 13 CBr 4 /PPh3, 14 EDC/HOBt, 15 and CDMT. 16 Additionally, mixed anhydride, 17 acid chloride, 18 acid fluoride 19 , and acyl benzotriazole 20 methods have also been used under varied reaction conditions.…”

Section: T R a C Tmentioning

confidence: 99%

Efficient synthesis of N-protected amino/peptide Weinreb amides from T3P and DBU

Sharnabai

Nagendra

Vishwanatha

et al. 2013

Tetrahedron Letters

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“…Peptide aldehydes, used extensively for the introduction of reduced peptide bonds into a peptide chain and in chemoselective ligation, are routinely produced using resins loaded with derivatives of Weinreb amide. The peptide aldehydes are released from these resins upon treatment with aluminum hydrides [93]. 11.12 SPPS of Peptides Modified at their C-Terminus j389…”

Section: Spps Of Peptides Modified At Their C-terminusmentioning

confidence: 99%