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Volumn 2, Issue 3, 2005, Pages 274-279

Synthesis of a dicarba-analog of octreotide keeping the type II' β-turn of the pharmacophore in water solution

Author keywords

NMR conformational study; Octreotide analog; Solid phase ring closing metathesis

Indexed keywords


EID: 39149096512     PISSN: 15701786     EISSN: None     Source Type: Journal    
DOI: 10.2174/1570178053765276     Document Type: Review
Times cited : (16)

References (41)
  • 14
    • 46149115539 scopus 로고    scopus 로고
    • +: 1231.8, calcd. 1231.6.
    • +: 1231.8, calcd. 1231.6.
  • 15
    • 46149093363 scopus 로고    scopus 로고
    • The mixture TFA/phenol/ethanedithiol/water (9 : 0.5 : 1 : 4) allowed the cleavage of the acetal bond and the full deprotection of the side chains from the Boc and tBu groups. The amide bond between the resin and the threoninol p-carboxybenzacetal was unaffected by this mixture.
    • The mixture TFA/phenol/ethanedithiol/water (9 : 0.5 : 1 : 4) allowed the cleavage of the acetal bond and the full deprotection of the side chains from the Boc and tBu groups. The amide bond between the resin and the threoninol p-carboxybenzacetal was unaffected by this mixture.
  • 27
    • 46149114518 scopus 로고    scopus 로고
    • To the on-resin linear octapeptide (390 mg, 0.2 mmol/g, suspended in DCM, a solution of (PCY3)2 Cl2Ru(CHPh, 0.5 equiv) in DCM was added and the mixture was heated, under stirring, at 40 °C for 50 h. The reaction was monitored by RP-HPLC and ESI-MS after microscale cleavage. The dried resin was then treated with 20% piperidine in DMF (4 × 4 mL, The cleavage from the resin and the side-chains deprotection were performed as described for compound 2. The lyophilized crude product was purified by twice repeated RP-HPLC (15 to 60% of B in 30 min, r.t, affording the pure cyclooctapeptide 3 (22 mg; 21% yield, calculated as a salt with two TFA molecules, Analytical HPLC performed at r.t, 15 to 35% of B in 20 min) gave a peak at Rt, 15.1 min. ESI-MS 981.8 [M, H, calcd. 981.5, 1003.7 M, Na, catcd. 1003.5
    • + (catcd. 1003.5).
  • 30
    • 46149115761 scopus 로고    scopus 로고
    • HN-2 signal was not observed neither at different pH (3, 5 and 7) nor at different temperatures 300-320 K
    • HN-2 signal was not observed neither at different pH (3, 5 and 7) nor at different temperatures (300-320 K).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.