Facile synthesis of 7-amino-4-carbamoylmethylcoumarin (ACC)-containing solid supports and their corresponding fluorogenic protease substrates

Bioorganic and Medicinal Chemistry Letters

Volumn 13, Issue 6, 2003, Pages 1033-1036

  Zhu, Qing ^a   Li, Dong B ^a   Uttamchandani, Mahesh ^a   Yao, Shao Q ^a  

^a NATIONAL UNIVERSITY OF SINGAPORE   (Singapore)

Author keywords

[No Author keywords available]

Indexed keywords

7 AMINO 4 CARBAMOYLMETHYLCOUMARIN; ALIPHATIC AMINE; COUMARIN DERIVATIVE; FUNCTIONAL GROUP; PROTEINASE; RESIN; UNCLASSIFIED DRUG;

ARTICLE; CONJUGATION; ENZYME SUBSTRATE; SYNTHESIS;

EID: 0037463803     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0960-894X(03)00087-8     Document Type: Article

References (16)

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13. 10Na 782.2690, found 782.2685.
14. 5 to give ACC-Gly-Wang resin. To a 20 mL conical test tube was added the above resin (0.1 g) and DMF (2 mL). Fmoc-Asp(tBu)-OH (0.288 g, 0.7 mmol), HATU (0.266 g, 0.7 mmol), and 2,4,6-collidine (85 mg, 0.7 mmol) were added, followed by shaking for three days to give Fmoc-Asp(tBu)-ACC-Gly-Wang resin. The resin was filtered and washed with DMF (3×20 mL). The substitution level of the resin was determined by Fmoc UV analysis to be 0.68 mmol/g (>95%).
15. LC was performed on a Waters™ 600 HPLC equipped with a Phenomenex RP-18 (5 μm, 4.6×250 mm) column using an acetontrile-water gradient (with 0.1% TFA). MS was run on an Electrospray mass spectrometer (Finnigan, USA).
16. Peptides were synthesized on Pioneer™ Peptide Synthesizer (PerSeptive Biosystems, USA) using standard Fmoc peptide chemistry with the HBTU/HOBt/DIEA coupling method.