3-(4-Hydroxymethylphenylsulfanyl)propanoic acid (HMPPA) as a new safety catch linker in solid phase peptide synthesis

Tetrahedron Letters

Volumn 47, Issue 32, 2006, Pages 5829-5832

  Erlandsson, Mikael ^a   Undén, Anders ^a  

^a STOCKHOLM UNIVERSITY   (Sweden)

Author keywords

[No Author keywords available]

Indexed keywords

3 (4 HYDROXYMETHYLPHENYLSULFANYL)PROPIONIC ACID; ACID; PROPIONIC ACID; RESIN; SULFIDE; SULFOXIDE; UNCLASSIFIED DRUG;

ARTICLE; COST EFFECTIVENESS ANALYSIS; OXIDATION; PEPTIDE SYNTHESIS; SOLID;

EID: 33745628742     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2006.04.138     Document Type: Article

References (30)

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24. 2 (0.63 ml) in TFE/DCM (2:1, 18 ml) for 4 h. 200 mg of the resin was transferred to another vessel and the first residue was attached by OAt ester activation (formed by premixing 10 equiv of Boc-Gly, HOAt and DIC, respectively, and 0.05 equiv DMAP in DCM for 30 min at 0 °C). The Boc group was removed by treatment for 20 min with TFA/DCM (1:1). Next, N-termini Fmoc protected residues were coupled by OBt ester activation. The Fmoc groups were removed by treatment for 20 min with 20% piperidine in DMF. 50 mg of the resin bound model peptide was treated for side-chain-to-side-chain lactamization by adding 2 equiv of BOP and HOBt, respectively, and 4.2 equiv of DIPEA in NMP to the side-chain deprotected peptide. The peptide was washed after 4 h and the procedure repeated once. The N-terminal Fmoc group was removed and the cyclic peptide, and 50 mg of the starting linear peptide, was resin cleaved by reductive acidolysis (0.2 M EDT and 0.1 M TMSBr in 3 ml TFA) for 2 h. The solution was filtered and washed with TFA (×3) and the solvents then removed in vacuo. The peptides were taken up in water and extracted with diethyl ether (×4). Both peptides were analyzed by RP-HPLC and MALDI-TOF. To estimate overall yields, the linear peptide was partially purified by semi-preparative RP-HPLC, lyophilized and analyzed gravimetrically, giving a total, overall yield of 52% as measured from initial resin loading.
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