Oxyma: An efficient additive for peptide synthesis to replace the benzotriazole-based HOBt and HOAt with a lower risk of explosion

Chemistry - A European Journal

Volumn 15, Issue 37, 2009, Pages 9394-9403

  Subirós Funosas, Ramon ^a,b   Prohens, Rafei ^b   Barbas, Rafael ^b   El Faham, Ayman ^a,c,d   Albericio, Fernando ^a,b  

^a INSTITUTE FOR RESEARCH IN BIOMEDICINE   (Spain)

^b UNIVERSITY OF BARCELONA   (Spain)

^c KING SAUD UNIVERSITY   (Saudi Arabia)

^d Alexandria University Faculty Of Science   (Egypt)

Author keywords

Additives; Calorimetry; Oximes; Peptide synthesis; Solidphase synthesis

Indexed keywords

BENZOTRIAZOLES; CARBODIIMIDES; COUPLING CONDITION; COUPLING EFFICIENCY; EXPLOSIVE PROPERTIES; OXIMES; PEPTIDE BONDS; PEPTIDE MODELS; PEPTIDE SYNTHESIS; RISK OF EXPLOSIONS; SOLIDPHASE SYNTHESIS;

ADDITIVES; CALORIMETERS; CALORIMETRY; COUPLING AGENTS; EXPLOSIVES; PEPTIDES; RESINS;

AMINES;

1 HYDROXY 7 AZABENZOTRIAZOLE; 1 HYDROXYBENZOTRIAZOLE; 1-HYDROXY-7-AZABENZOTRIAZOLE; 1-HYDROXYBENZOTRIAZOLE; ACYL CARRIER PROTEIN; ACYL CARRIER PROTEIN (65 74); ACYL CARRIER PROTEIN (65-74); BENZOTRIAZOLE; HETEROCYCLIC COMPOUND; OXYMA; PEPTIDE; PEPTIDE FRAGMENT; PREGNANE DERIVATIVE; TRIAZOLE DERIVATIVE;

AMINO ACID SEQUENCE; ARTICLE; CALORIMETRY; CHEMISTRY; SYNTHESIS;

ACYL CARRIER PROTEIN; AMINO ACID SEQUENCE; AZA COMPOUNDS; CALORIMETRY; PEPTIDE FRAGMENTS; PEPTIDES; PREGNADIENES; TRIAZOLES;

EID: 70349275493     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200900614     Document Type: Article

References (41)

1. Abbreviations not defined in text: Aib, a-aminoisobutyric acid; ACP, acyl carrier protein decapeptide (65-74); AM-PS, aminomethyl-polystyrene resin; ARC, accelerating rate calorimetry; 6-C1HOBt, 6-chloro-l-hydroxybenzotriazole; DIC, N ,N-diisopropylcarbodiimide; DIEA, N, N-diisopropylethylamine ; DMF, N, N-dimethylformamide; DSC, Differential Scanning Calorimetry; HATU, N[(dimethylamino)-l H-l,2,3-triazolo[4,5-b]pyridin-l-yl-methylene)- Nmethylmethanaminium hexafluorophosphate N-oxide; HBTU, N[(l H-benzotriazol-l-yl)-(dimethylamino)methylene]N-methylmethanaminium hexafluorophosphate N-oxide; HCTU, N-[(1H-6-chlorobenzotriazol-l-yl) (dimethylamino)methylene]-N-methylmethanaminium hexafluorophosphate N-oxide; HOAt, 7-aza-l-hydroxybenzotriazole; HOBt, 1-hydroxybenzotriazole; HODhbt, 3-hydroxy-3,4-dihydro-4-oxo-l,2,3-benzotriazine; HOPO, 2-hydroxypyridine-N-oxide ; HOPfp, pentafluorophenol; HOSu, N-hydroxysuccinimide; NMP, Nmethyl-2-pyrrolidinone ; PyAOP, azabenzotriazol-l-yl-N-oxy-tris(pyrrolidino) phosphonium hexafluorophosphate; PyBOP, benzotriazoll-yl-N-oxy-tris(pyrrolidino) phosphonium hexafluorophosphate; PyClock, 6-chloro-benzotriazol-l-yl-N-oxy-tris- pyrrolidino-phosphonium hexafluorophosphate; TBTU, N-[(lH-benzotriazol-l-yl) (dimethylamino)methylene]N-methylmethanaminium tetrafluoroborate N-oxide; TCTU, N-[(1H-6-chlorobenzotriazol-l-yl)(dimethylamino)methylene]-N- methylmethanaminium tetrafluoroborate N-oxide ; TFA, trifluoroacetic acid; Z, benzyloxycarbonyl. Amino acids and peptides are abbreviated and designated following the rules of the IUPAC-IUB Commission of Biochemical Nomenclature (J. Biol. Chem. 1972, 247, 977).
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