N,N'-Diacetyl-lysinyl-D-alanyl-D-lactic acid
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N,N'-Diacetyl-lysinyl-D-alanyl-D-lactic acid

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A depsipeptide substrate for penicillin-sensitive D-alanine carboxypeptidases (DD-carboxypeptidases).

Category
Others
Catalog number
BAT-015712
CAS number
65882-12-4
Molecular Formula
C16H27N3O7
Molecular Weight
373.40
N,N'-Diacetyl-lysinyl-D-alanyl-D-lactic acid
IUPAC Name
2-[2-(2,6-diacetamidohexanoylamino)propanoyloxy]propanoic acid
Synonyms
Nalpha,Nepsilon-Diacetyl-Lys-D-Ala-D-lactic acid
Appearance
White Powder
Purity
>99%
Density
1.2±0.1 g/cm3
Boiling Point
740.5±60.0 °C at 760 mmHg
Sequence
Ac-DL-Lys(Ac)-DL-Ala-DL-OAla-OH
Storage
-20°C
InChI
InChI=1S/C16H27N3O7/c1-9(16(25)26-10(2)15(23)24)18-14(22)13(19-12(4)21)7-5-6-8-17-11(3)20/h9-10,13H,5-8H2,1-4H3,(H,17,20)(H,18,22)(H,19,21)(H,23,24)
InChI Key
LOEWINUIHJAOMZ-UHFFFAOYSA-N
Canonical SMILES
CC(C(=O)OC(C)C(=O)O)NC(=O)C(CCCCNC(=O)C)NC(=O)C
1. Recent Trends in Photocatalytic Enantioselective Reactions
Renu Verma, Palvi Jindal, Jagdish Prasad, S L Kothari, Narendra Pal Lamba, Anshu Dandia, Rama Kanwar Khangarot, Manmohan Singh Chauhan Top Curr Chem (Cham). 2022 Sep 16;380(6):48. doi: 10.1007/s41061-022-00402-9.
Enantioselective synthesis through photocatalysis is one of the highly preferred approaches towards preparation of optically active compounds. This review elaborates and critically analyzes the different strategies of photocatalytic enantioselective reactions through H-bonding, transition metal catalysis, phase-transfer catalysis (PTC), chiral Lewis acid catalysis, N-heterocyclic carbene catalysis, and amine catalysis, and also explores ion pairs. In addition, it explains the different catalysis modes with multifunctional approaches for enantioselective photocatalytic reactions.
2. Recent Developments in Arylation of N-Nucleophiles via Chan-Lam Reaction: Updates from 2012 Onwards
Fahimeh Abedinifar, Mohammad Mahdavi, Elham Babazadeh Rezaei, Mehdi Asadi, Bagher Larijani Curr Org Synth. 2022;19(1):16-30. doi: 10.2174/1570179417666210105120706.
''Chan-Evans-Lam'' (CEL) reaction is the copper-mediated cross-coupling of N-nucleophiles with boronic acids that was independently reported in 1998 by Chan, Evans, and Lam for the first time. This reaction is accomplished at room temperature with a remarkably wide range of nucleophiles. In the recent decade, it has been particularly attractive as a convenient method for constructing the various C- N bonds in organic synthesis. Therefore, a comprehensive survey through all reported process was crucial. In this review, we summarized research progress about N-Arylation, based on the type of N-nucleophile involved in this reaction and catalysts from 2012 onwards.
3. Natural Products Containing 'Rare' Organophosphorus Functional Groups
Janusz J Petkowski, William Bains, Sara Seager Molecules. 2019 Feb 28;24(5):866. doi: 10.3390/molecules24050866.
Phosphorous-containing molecules are essential constituents of all living cells. While the phosphate functional group is very common in small molecule natural products, nucleic acids, and as chemical modification in protein and peptides, phosphorous can form P⁻N (phosphoramidate), P⁻S (phosphorothioate), and P⁻C (e.g., phosphonate and phosphinate) linkages. While rare, these moieties play critical roles in many processes and in all forms of life. In this review we thoroughly categorize P⁻N, P⁻S, and P⁻C natural organophosphorus compounds. Information on biological source, biological activity, and biosynthesis is included, if known. This review also summarizes the role of phosphorylation on unusual amino acids in proteins (N- and S-phosphorylation) and reviews the natural phosphorothioate (P⁻S) and phosphoramidate (P⁻N) modifications of DNA and nucleotides with an emphasis on their role in the metabolism of the cell. We challenge the commonly held notion that nonphosphate organophosphorus functional groups are an oddity of biochemistry, with no central role in the metabolism of the cell. We postulate that the extent of utilization of some phosphorus groups by life, especially those containing P⁻N bonds, is likely severely underestimated and has been largely overlooked, mainly due to the technological limitations in their detection and analysis.
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