2015
DOI: 10.1002/anie.201505379
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Chemical Synthesis of the 20 kDa Heme Protein Nitrophorin 4 by α‐Ketoacid‐Hydroxylamine (KAHA) Ligation

Abstract: The chemical synthesis of the 184-residue ferric heme-binding protein nitrophorin 4 was accomplished by sequential couplings of five unprotected peptide segments using α-ketoacid-hydroxylamine (KAHA) ligation reactions. The fully assembled protein was folded to its native structure and coordinated to the ferric heme b cofactor. The synthetic holoprotein, despite four homoserine residues at the ligation sites, showed identical properties to the wild-type protein in nitric oxide binding and nitrite dismutase rea… Show more

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Cited by 29 publications
(17 citation statements)
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“…We chose this site because this disconnection resulted in two similarly sized peptide segments and our previous studies have shown that replacement of Ser/Thr residue with homoserine (Hse, T § ) do not affect the folding or biological activity of synthetic proteins compared to wild type references. 18 20 …”
Section: Resultsmentioning
confidence: 99%
“…We chose this site because this disconnection resulted in two similarly sized peptide segments and our previous studies have shown that replacement of Ser/Thr residue with homoserine (Hse, T § ) do not affect the folding or biological activity of synthetic proteins compared to wild type references. 18 20 …”
Section: Resultsmentioning
confidence: 99%
“…In addition, small proteins and variants thereof have been synthesized through α-Ketoacidhydroxylamine (KAHA) ligations including C-terminal modifications of the Ubiquitin-fold modifier 1 (UFM1), glucagonlike peptide-1 (GLP-1), variants of interleukin-2 (IL-2), ubiquitinconjugating enzyme 9 (Ubc9), ubiquitin-conjugating enzyme H5a (UbcH5a), the Titan protein domain, human insulin variants, derivatives of interferon-induced transmembrane protein 3 nitrophorin and others (Scheme 30). [67][68][69][70][71][72][73][74][75][76][77] Fmoc or Boc Scheme 32. Synthesis of epoxides from aldehydes by C-C bond formation using selenium ylides 79…”
Section: Accepted Manuscriptmentioning
confidence: 99%
“…Scheme 30. Synthesis of small proteins and natural cyclopeptides based on C-acylation of sulfur ylides[67][68][69][70][71][72][73][74][75][76][77] 4 Miscellaneous ylides as acyl anion equivalents Besides phosphorus and sulfur ylides, ammonium ylides were reported to behave as acyl anion equivalents that undergo reactions with active electrophiles leading to new C-C bonds. Wang et.…”
mentioning
confidence: 99%
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“…Theu se of 5-oxaproline results in the introduction of homoserine,anon-canonical amino acid, at the ligation site.W hen carefully chosen, we have found that this is an innocuous mutation of many residues and have shown that it does not disturb folding or biological activity. [18] Thes ynthetic route allows facile incorporation of key posttranslational modifications,i ncluding phosphorylation and the attachment of afluorescent dye.This work establishes access to homogenous IFITM3 and will enable further studies on its structure and mode of action.…”
mentioning
confidence: 99%