51782-87-7Relevant academic research and scientific papers
Organocatalyzed Asymmetric Aldol Reaction of α-Keto Amides with A Tripeptide Catalyst
Kon, Kazumasa,Takai, Hiromu,Kobayashi, Takumu,Kohari, Yoshihito,Murata, Miki
, p. 829 - 832 (2021)
An organocatalyzed asymmetric aldol reaction of α-keto amides was developed. An N-terminal 4- trans -siloxyproline-based tripeptide with an l - tert -leucine unit adjacent to the 4- trans -siloxyproline residue was used to catalyze the reaction between various α-keto amides and acetone, to produce the corresponding aldol adducts with up to 99% yield and 91% ee.
Unnatural tripeptide as highly enantioselective organocatalyst for asymmetric aldol reaction of isatins
Kon, Kazumasa,Kohari, Yoshihito,Murata, Miki
supporting information, p. 415 - 418 (2019/01/05)
The development of unnatural tripeptides as highly enantioselective organocatalysts for the asymmetric aldol reaction of isatins was achieved. H-Pro-Gly-D-Ala-OH with the D-alanine residue as the C-terminal amino acid residue expressed the best enantioselectivity. The H-Pro-Gly-D-Ala-OH-catalyzed reaction of isatins gave various aldol adducts with up to 93% yield and up to 97% ee. Investigation of the transition state via DFT calculation revealed that high optical purity was realized by the D-alanine controlled steric environment.
Dynamic combinatorial libraries of hydrazone-linked pseudo-peptides: Dependence of diversity on building block structure and chirality
Liu, Jingyuan,West, Kevin R.,Bondy, Chantelle R.,Sanders, Jeremy K. M.
, p. 778 - 786 (2008/03/14)
Expanding on our earlier building block architecture [(MeO) 2CH-Linker-Pro-X-NHNH2 where X = Phe, Cha], we have produced a series of new pseudo-dipeptides [(MeO)2CH-Linker-Pro-X- NHNH2 where X = Val, Leu, Ile, A
tert-Butyloxycarbonyl and Benzyloxycarbonyl Amino Acid Fluorides. New, Stable Rapid-Acting Acylating Agents for Peptide Synthesis
Carpino, Louis A.,Mansour, El-Sayed M. E.,Sadat-Aalaee, Dean
, p. 2611 - 2614 (2007/10/02)
A new class of rapid-acting acylating agents, α-BOC and Z amino acid fluorides are obtained as stable, often crystalline, compounds by treatment of the protected amino acid cyanuric fluoride.
KINETICS OF THE ALKALINE HYDROLYSIS OF SEVERAL N-BENZYLOXYCARBONYLDIPEPTIDE METHYL AND ETHYL ESTERS
Hoogwater, D. A.,Peereboom, M.
, p. 5325 - 5332 (2007/10/02)
The reaction rates of the alkaline hydrolysis of synthesized N-protected dipeptide methyl and ethyl esters were studied systematically.From the kinetic data the energies of activation, the pre-exponential factors and the reference values at 40 deg C were calculated.The rate of hydrolysis shows to be strongly dependent on the C-terminal amino acid in the sequence Gly >> Ala/Met/Phe > Leu >> Val/Pro.Surprisingly the N-terminal amino acid also exerts an effect, but in a different sequence.N-Terminal Phe in particular shows a relative accelerating effect.Remarkable is the significantly faster ester hydrolysis of glycine containing dipeptide ethyl esters in ethanol/water compared to the corresponding methyl esters in methanol/water.
TOTAL SYNTHESIS OF (+)- AND (-)-NORSECURININE
Jacobi, Peter A.,Blum, Charles A.,DeSimone, Robert W.,Udodong, Uko E. S.
, p. 7173 - 7176 (2007/10/02)
(-)-Norsecurinine (1a) has been prepared in a stereospecific fashion beginning with the acetylenic oxazole 18.Diels-Alder cyclization of 18 afforded the furanoketone 19, which was transformed in five steps to the butenolide mesylate 24.Transannular alkyla
Alkylamides of carboxyalkanoyl peptides and method for preparation thereof
-
, (2008/06/13)
A method is described for the preparation of novel alkylamides of carboxyalkanoyl peptides of the formula STR1 wherein R is an aralky or an alkyl group of 1-5 carbon atoms, A is a residue of peptidically bound proline or alanine, B is a straight bond or a
