74481-57-5Relevant articles and documents
Total synthesis and structure assignment of papuamide B, A potent marine cyclodepsipeptide with anti-HIV properties
Xie, Weiqing,Ding, Derong,Zi, Weiwei,Li, Guangyu,Ma, Dawei
, p. 2844 - 2848 (2008/12/23)
Synthesis in stereo: The first total synthesis of papuamide B, a cyclic peptide isolated from a marine sponge, has been achieved. The configuration of three stereogenic centers of its dienoic acid unit has been established by comparison to a series of ste
Aziridine-2-carboxylic acid-containing peptides: Application to solution- and solid-phase convergent site-selective peptide modification
Galonic, Danica P.,Ide, Nathan D.,Van Der Donk, Wilfred A.,Gin, David Y.
, p. 7359 - 7369 (2007/10/03)
The development of a method for site- and stereoselective peptide modification using aziridine-2-carboxylic acid-containing peptides is described. A solid-phase peptide synthesis methodology that allows for the rapid generation of peptides incorporating the aziridine residue has been developed. The unique electrophilic nature of this nonproteinogenic amino acid allows for site-selective conjugation with various thiol nucleophiles, such as anomeric carbohydrate thiols, farnesyl thiol, and biochemical tags, both in solution and on solid support. This strategy, combined with native chemical ligation, provides convergent and rapid access to complex thioglycoconjugates.
Conjugation of selenols with aziridine-2-carboxylic acid-containing peptides
Ide, Nathan D.,Galoni?, Danica P.,Van Der Donk, Wilfred A.,Gin, David Y.
, p. 2011 - 2014 (2007/10/03)
The addition of PhSeH to aziridine-2-carboxylic acid containing peptides is described, thus expanding the scope of nucleophiles for the opening of this class of electrophilic peptide substrates. The process offers a new strategy for the generation of usef
Studies on 2-Aziridinecarboxylic Acid.IV.Total Synthesis of Actinomycin D (C1) via Ring-opening Reaction of Aziridine
Tanaka, Takumi,Nakajima, Kiichiro,Okawa, Kenji
, p. 1351 - 1355 (2007/10/02)
Actinomycin D (C1) has been synthesized by a route involving the ester formation between two peptide fragments, (2S,3S)-1-(2-nitro-3-benzyloxy-4-methylbenzoyl)-3-methyl-2-aziridiecarbonyl-D-valylproline t-butyl ester and N-benzyloxycarbonylsarc