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Volumn 9, Issue 13, 2007, Pages 2469-2472

Solid-phase synthesis of carboxylic and oxamic acids via OsO 4/NaIO4/HMTA-mediated oxidative cleavage of acetylenic peptides

(3) Nielsen, Thomas E a Le Quement, Sebastian T a Meldal, Morten a

a CARLSBERG LABORATORY (Denmark)

Author keywords

[No Author keywords available]

Indexed keywords

3 HYDROXY 4 METHYLTETRADECANOIC ACID; 3-HYDROXY-4-METHYLTETRADECANOIC ACID; CARBOXYLIC ACID; MYRISTIC ACID DERIVATIVE; OSMIUM TETRAOXIDE; OXAMIC ACID; PEPTIDE; SODIUM IODIDE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMISTRY; OXIDATION REDUCTION REACTION; SYNTHESIS;

CARBOXYLIC ACIDS; CATALYSIS; MYRISTIC ACIDS; OSMIUM TETROXIDE; OXAMIC ACID; OXIDATION-REDUCTION; PEPTIDES; SODIUM IODIDE;

EID: 34547211174 PISSN: 15237060 EISSN: None Source Type: Journal
DOI: 10.1021/ol070693p Document Type: Article

Times cited : (17)

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- Representative Procedure for Oxidatlve Cleavage of Acetylenic Peptides. A suspension of solid-supported alkyne 6 (1.0 equiv, 0,006 mmol, 20 mg, NaIO4 (10.0 equiv, 0,06 mmol, 13 mg, and HMTA (5.0 equiv, 0,03 mmol, 4 mg) in THF/water (1:1) was shaken for 10 min, after which time OsO 4 (0.05 equiv, 0,3 μmol, 4μL of a 2.5 wt, solution in 2-methyl-2-propanol) was added. The initially reddish reaction mixture was shaken for 16 h at 20 °C. Subsequently, the resin was washed with water (×6, 10% TFA (aq, ×3, water (×6, DMF (×6, and CH2Cl2 (×6, The resin was lyophilized to remove all traces of solvent. For release of material 7 from the solid phase, beads were treated with 0.1 M NaOH (aq) for 2 h, then neutralized with the equimolar amount of 0.1 M HCl aq, and finally diluted with CH3CN. The resulting solution was filtered and analyzed by RP-HPLC/MS
- 3CN. The resulting solution was filtered and analyzed by RP-HPLC/MS.

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