Racemization studies of Fmoc-Ser(tBu)-OH during stepwise continuous- flow solid-phase peptide synthesis

Tetrahedron Letters

Volumn 39, Issue 46, 1998, Pages 8529-8532

  Di Fenza, Armida ^a   Tancredi, Mariella ^a   Galoppini, Claudia ^a   Rovero, Paolo ^a  

^a CNR   (Italy)

Author keywords

Amino acids and derivatives; Racemization; Solid phase synthesis

Indexed keywords

9 FLUORENYLMETHYL CHLOROFORMATE; AMINO ACID; AMINO ACID DERIVATIVE; COLLIDINE; GLYCINE; PHENYLALANINE; SERINE; TRIPEPTIDE;

PEPTIDE SYNTHESIS; PROTEIN ASSEMBLY; REVIEW; SOLID PHASE EXTRACTION; STEREOCHEMISTRY; STRUCTURE ACTIVITY RELATION;

EID: 0032512076     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)01891-7     Document Type: Article

References (22)

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8. 4. Abbreviations are in accord with the recommendation of the IUPAC-IUB Commission on Biochemical Nomenclature (J. Biol. Chem. 1972, 247, 977). All amino acids are in the L configuration unless otherwise specified. Other abbreviations: Boc, t-butyloxycarbonyl; DMF, dimethylformamide; EI-MS, electrospray ionization mass spectrometry; Fmoc, 9-fluorenylmethoxy-carbonyl; HATU, (7-azabenzotriazol-1-yloxy)tris(pyrrolidino)phosphonium hexafluorophosphate; HBTU, N-[[(dimethylamino)-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl]methylene]-N-methylmethanaminium hexafluorophosphate N-oxide; HOAt, 7-aza-1-hydroxybenzotriazole; HOBt, 1-hydroxybenzotriazole; NMM, N-methylmorpholine; RP-HPLC, reverse-phase high performance liquid chromatography; SPPS, solid-phase peptide synthesis; TMP, 2,4,6-trimethylpyridine or collidine.
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11. 6. TentaGel S AM is a polystyrene-supported polyoxyethylene resin with the 5-(4-amino-methyl-3,5-dimethoxyphenoxy) valeric acid linker for the synthesis of peptide amides.
12. 18 column 0.46 × 15 cm; eluant A: 0.1% TFA/water, eluant B: 0.1% TFA/acetonitrile; gradient from 5% to 65% B over 20 min; flow 1 ml/min; detection UV, 210 nm.
13. 8. Standard peptides were synthesized on a Milligen 9050 automated synthesizer, starting from 0.5 g of TentaGel S AM resin (0.25 mmol/g); Fmoc-Phe-OH, Fmoc-Ser(tBu)-OH or Fmoc-D-Ser(tBu)-OH and Fmoc-Gly-OH were coupled using HBTU/HOBt/NMM activation (4:4:8 equiv.) in DMF (15 min at 8 ml/min). Fmoc removal was carried out with 20% piperidine in DMF (v/v) for 3.5 min at 8 ml/min. Final deprotection and cleavage was obtained using reagent K for 90 min at room temperature.
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