957753-07-0Relevant articles and documents
A rapid and efficient one-pot method for the reduction of N-protected α-amino acids to chiral α-amino aldehydes using CDI/DIBAL-H
Ivkovic, Jakov,Lembacher-Fadum, Christian,Breinbauer, Rolf
supporting information, p. 10456 - 10460 (2015/11/10)
N-Protected amino acids can be easily converted into chiral α-amino aldehydes in a one-pot reaction by activation with CDI followed by reduction with DIBAL-H. This method delivers Boc-, Cbz- and Fmoc-protected amino aldehydes from proteinogenic amino acids in very good isolated yields and complete stereointegrity.
A traceless approach to amide and peptide construction from thioacids and dithiocarbamate-terminal amines
Chen, Wenteng,Shao, Jiaan,Hu, Miao,Yu, Wanwan,Giulianotti, Marc A.,Houghten, Richard A.,Yu, Yongping
, p. 970 - 976 (2013/06/05)
A novel and traceless strategy has been devised that allows a coupling of thioacids and dithiocarbamate-terminal amines. This strategy had been assumed to be dependent on the attachment of a functional equivalent of a cysteine side chain in earlier native chemical ligation approaches. This approach enables the traceless removal of CS2 to directly generate the desired amide bond and is compatible with a range of unprotected side chains of amino acid. The ability to produce amide or peptides by a traceless removal of the auxiliary is a significant virtue of the method. Meanwhile, the application of this new peptide-bond-forming reaction to the synthesis of novel endomorphin (EM) derivatives with various binding potencies was realized.
Se -(9-fluorenylmethyl) selenoesters; Preparation, reactivity, and use as convenient synthons for selenoacids
Fecourt, Fabien,Delpech, Bernard,Melnyk, Oleg,Crich, David
, p. 3758 - 3761 (2013/08/23)
Se-(9-Fluorenylmethyl) selenoesters are readily prepared, stable precursors to selenocarboxylates, which they liberate on treatment with DBU. Fm selenoesters are compatible with the use of TFA for the removal of Boc groups and with simple peptide bond for
The synthesis of functionalised peptides using α-lithio quinuclidine N-oxide (Li-QNO)
O'Neil, Ian A.,Bhamra, Inder
supporting information; experimental part, p. 3635 - 3638 (2009/09/30)
Deprotonation of protected peptides using lithiated quinuclidine N-oxide (Li-QNO) as a base at 0 °C, followed by addition of an alkyl halide gives C-alkylated peptide derivatives in good yield.
Comprehensive study of sansalvamide A derivatives and their structure-activity relationships against drug-resistant colon cancer cell lines
Otrubova, Katerina,Lushington, Gerald,Vander Velde, David,McGuire, Kathleen L.,McAlpine, Shelli R.
, p. 530 - 544 (2008/09/18)
We report an extensive structure-activity relationship (SAR) of 62 compounds active against two drug-resistant colon cancer cell lines. Our comprehensive evaluation of two generations of compounds utilizes SAR, NMR, and molecular modeling to evaluate the
Amino acid and peptide synthesis and functionalization by the reaction of thioacids with 2,4-dinitrobenzenesulfonamides
Crich, David,Sana, Kasinath,Guo, Songpo
, p. 4423 - 4426 (2008/03/12)
(Formula Presented) Readily prepared amino thioacids react at room temperature in DMF in the presence of cesium carbonate with 2,4- dinitrobenzenesulfonamides to give amides. When the sulfonamide is derived from an amino acid the method results in peptide bond formation, whereas the use of carbohydrate derived sulfonamides gives neoglycoconjugates.
Conformational effects in reversed-phase liquid chromatographic separation of diastereomers of cyclic dipeptides
Funasaki, Noriaki,Hada, Sakae,Neya, Saburo
, p. 1861 - 1867 (2007/10/02)
The capacity factors, k′, of 11 cyclic dipeptides (X-Y) including diastereomers have been determined on an RP-HPLC column in 30% and 50% methanol and 10%, 30%, and 50% acetonitrile solutions. These factors are roughly correlated with hydrophobic parameters, such as octanol-water partition coefficients estimated and k′ values for alcohols. For a pair of diastereomers of cyclic (L-X-L-Phe) and (L-X-D-Phe) derivatives k′LL is larger than k′LD and for cyclic (D-Ala-L-Trp) and (L-Ala-L-Trp) k′LL is smaller than k′DL, particularly in highly aqueous solutions. These elution orders can be well predicted by the holistic molecular surface area approach which takes into account the folded structures of cyclic dipeptides. The present results will be useful for prediction of the log k′ values of larger peptides and the hydrophobicity and related properties of peptides.
