3-Hydroxy-4-oxo-3,4-dihydro-5-azabenzo-1,2,3-triazene

The known but long-neglected compound HODhat was shown to be in certain situations a useful peptide coupling additive. Uronium and phosphonium salts with HODhat built into the system were also useful stand-alone coupling reagents. Comparisons with related additives and coupling reagents showed that...

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Bibliographic Details
Published inJournal of organic chemistry Vol. 69; no. 1; pp. 54 - 61
Main Authors Carpino, Louis A, Xia, Jusong, El-Faham, Ayman
Format Journal Article
LanguageEnglish
Published Washington, DC American Chemical Society 09.01.2004
Subjects
Chemistry
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings
Magnetic Resonance Spectroscopy
Organic chemistry
Preparations and properties
Spectrophotometry, Ultraviolet
Triazines - chemical synthesis
Triazines - chemistry
Decapeptide
Peptides
Molecular assembly
Triazene derivatives
Phosphonium
Chemical synthesis
Modeling
Chemical coupling
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Summary:The known but long-neglected compound HODhat was shown to be in certain situations a useful peptide coupling additive. Uronium and phosphonium salts with HODhat built into the system were also useful stand-alone coupling reagents. Comparisons with related additives and coupling reagents showed that the new systems were sometimes more and sometimes less effective than previously described systems in the case of stepwise and segment couplings. Applications to assembly of the model decapeptide ACP showed that HDATU was far more effective than HDTU and more effective than HATU under some conditions.
Bibliography:ark:/67375/TPS-J8B908S7-7
Abbreviations:  Aib = α-aminoisobutyric acid; ACP = acyl carrier protein decapeptide (65−74); CIP = 2-chloro-1,3-dimethyl-2-imidazolidinium hexafluorophosphate; DCM = dichloromethane; DIC = diisopropylcarbodiimide; DIEA = N,N-diisopropylethylamine; EDC = 1-ethyl-3-(3‘-(dimethylamino)propyl)carbodiimide; HAPyU = 1-(l-pyrrolidinyl-lH-1,2,3-triazolo[4,5-b]pyridin-l-ylmethylene)-N-methylmethanaminium hexafluorophosphate N-oxide; HATU = N-[(dimethylamino)-1H-1,2,3-triazolo[4,5-b]pyridin-l-ylmethylene)-N-methylmethana-minium hexafluorophosphate N-oxide; HBTU = N-[(1H-benzotriazol-l-yl)(dimethylamino)methylene]-N-methylmethanaminium hexafluorophosphate N-oxide; HDTU = O-(3,4-dihydro-4-oxo-l,2,3-benzotriazin-3-yl)-1,1,3,3-tetramethyluromium hexafluorophosphate; Pfp = penta-fluorophenyl; Phg = α-phenylglycine; PyBrOP = bromotris(pyrrolidino)phosphonium hexafluorophosphate; PyClU = bis(tetramethylene)chlorofomamidinium hexafluorophosphate; TEA = triethylamine; TCFH = tetramethylchloroformamidinium hexafluorophosphate; TCM = trichloromethane = chloroform; TFE = trifluoroethanol; TMP = 2,4,6-trimethylpyridine (collidine
istex:E740AA6E0FDE77F8FBB1E94C21FB12228287B486
ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:0022-3263
1520-6904
DOI:10.1021/jo030017a