Category: 2418-95-3

Tian, Zi-You published the artcileA moisture-tolerant route to unprotected α/β-amino acid N-carboxyanhydrides and facile synthesis of hyperbranched polypeptides, SDS of cas: 2418-95-3, the publication is Nature Communications (2021), 12(1), 5810, database is CAplus and MEDLINE.

A great hurdle in the production of synthetic polypeptides lies in the access of N-carboxyanhydrides (NCA) monomers, which requires dry solvents, Schlenk line/gloveboxe, and protection of side-chain functional groups. Here we report a robust method for preparing unprotected NCA monomers in air and under moisture. The method employs epoxy compounds as ultra-fast scavengers of hydrogen chloride to allow assisted ring-closure and prevent NCA from acid-catalyzed decomposition under moist conditions. The broad scope and functional group tolerance of the method are demonstrated by the facile synthesis of over 30 different α/β-amino acid NCAs, including many otherwise inaccessible compounds with reactive functional groups, at high yield, high purity, and up to decagram scales. The utility of the method and the unprotected NCAs is demonstrated by the facile synthesis of two water-soluble polypeptides that are promising candidates for drug delivery and protein modification. Overall, our strategy holds great potential for facilitating the synthesis of NCA and expanding the industrial application of synthetic polypeptides.

Nature Communications published new progress about 2418-95-3. 2418-95-3 belongs to amides-buliding-blocks, auxiliary class Chiral,Carboxylic acid,Amine,Aliphatic hydrocarbon chain,Ester,Amino acide derivatives, name is H-Lys(Boc)-OH, and the molecular formula is C3H6BrNaO3S, SDS of cas: 2418-95-3.

Referemce:
https://en.wikipedia.org/wiki/Amide,
Amide – an overview | ScienceDirect Topics

Wang, Jiawen published the artcileChiral phosphoric acid-catalyzed stereodivergent synthesis of trisubstituted allenes and computational mechanistic studies, Computed Properties of 2418-95-3, the publication is Nature Communications (2020), 11(1), 5527, database is CAplus and MEDLINE.

Here-in, an enantioselective and diastereodivergent synthesis of trisubstituted allenes I (R = Et, nBu, Bn, etc.; R¹ = nBu, Ph, thiophen-3-yl, etc.; R² = Ph, 4-chlorophenyl, cyclohexyl, etc.; R³ = Me, Et, n-Pr, n-Bu, i-Bu) and II by asym. additions of oxazolones III to activated 1,3-enynes R²CH:C(CCR¹)C(O)R³ enabled by chiral phosphoric acid (CPA) catalysis where the divergence of the allenic axial stereogenicity is realized by modifications of CPA catalysts was reported. D. functional theory (DFT) calculations are performed to elucidate the origin of diastereodivergence by the stacking- and stagger-form in the transition state (TS) of allene formation step, as well as to disclose a Munchnone-type activation mode of oxazolones II under Bronsted acid catalysis.

Nature Communications published new progress about 2418-95-3. 2418-95-3 belongs to amides-buliding-blocks, auxiliary class Chiral,Carboxylic acid,Amine,Aliphatic hydrocarbon chain,Ester,Amino acide derivatives, name is H-Lys(Boc)-OH, and the molecular formula is C3H6O2, Computed Properties of 2418-95-3.

Referemce:
https://en.wikipedia.org/wiki/Amide,
Amide – an overview | ScienceDirect Topics

Hankore, Erome Daniel published the artcileGenetic incorporation of noncanonical amino acids using two mutually orthogonal quadruplet codons, Safety of H-Lys(Boc)-OH, the publication is ACS Synthetic Biology (2019), 8(5), 1168-1174, database is CAplus and MEDLINE.

Genetic incorporation of noncanonical amino acids has emerged as a powerful tool for the study of protein structure and function. While the three triplet nonsense codons have been widely explored, quadruplet codons have attracted attention for the potential of creating addnl. blank codons for noncanonical amino acid mutagenesis. Here we demonstrated for the first time that two orthogonal quadruplet codons could be used to simultaneously encode two different noncanonical amino acids within a single protein in bacterial cells. To achieve this, we fine-tuned the interaction between aminoacyl-tRNA synthetase and tRNA, which afforded up to 21-fold improvement in quadruplet codon decoding efficiency. This work represents a significant step toward the use of multiple quadruplet codons for noncanonical amino acid mutagenesis. Simultaneous incorporation of two or more noncanonical amino acids is of significant importance for biol. applications that can benefit from multiple unique functional groups, such as fluorescence resonance energy transfer and NMR studies, and ultimately for the synthesis of completely unnatural biopolymers as new biomaterials.

ACS Synthetic Biology published new progress about 2418-95-3. 2418-95-3 belongs to amides-buliding-blocks, auxiliary class Chiral,Carboxylic acid,Amine,Aliphatic hydrocarbon chain,Ester,Amino acide derivatives, name is H-Lys(Boc)-OH, and the molecular formula is C11H22N2O4, Safety of H-Lys(Boc)-OH.

Referemce:
https://en.wikipedia.org/wiki/Amide,
Amide – an overview | ScienceDirect Topics

Wu, Yue-Ming published the artcileFacile synthesis of high molecular weight polypeptides via fast and moisture insensitive polymerization of alpha-amino acid N-carboxyanhydrides, Category: amides-buliding-blocks, the publication is Chinese Journal of Polymer Science (2020), 38(10), 1131-1140, database is CAplus.

Polypeptides have been widely utilized in the fields of biomaterials and biomedicine. Ever since N-carboxyanhydride (NCA) was reported by Hermann Leuchs in 1906, ring-opening polymerization of NCAs has been extensively used to prepare polypeptides. Despite continuous innovations, it is still challenging to synthesize polypeptides in high mol. weight efficiently. To address this challenge, we developed KHMDS/NaHMDS initiated fast NCA polymerization that is also moisture tolerant, open-flask amenable and terminal tunable. This NCA polymerization was able to proceed in most common solvents and meet the solubility requirement of variable NCA monomers and corresponding polypeptides. KHMDS can initiate γ-benzyl-L-glutamate-N-carboxyanhydride (BLG NCA) polymerization in a reaction rate 92 times faster than does hexylamine and 80 times faster than does triethylamine. This NCA polymerization also demonstrated easy and fast synthesis of gram-scale long chain polypeptides in an open flask.

Chinese Journal of Polymer Science published new progress about 2418-95-3. 2418-95-3 belongs to amides-buliding-blocks, auxiliary class Chiral,Carboxylic acid,Amine,Aliphatic hydrocarbon chain,Ester,Amino acide derivatives, name is H-Lys(Boc)-OH, and the molecular formula is C7H6Cl2, Category: amides-buliding-blocks.

Referemce:
https://en.wikipedia.org/wiki/Amide,
Amide – an overview | ScienceDirect Topics

Fan, Wei published the artcileIncreasing time on target: utilization of inhibitors of cysteine cathepsins to enhance the tumor retention of receptor-targeted agents, Application In Synthesis of 2418-95-3, the publication is Chemical Communications (Cambridge, United Kingdom) (2018), 54(80), 11268-11271, database is CAplus and MEDLINE.

We report a strategy of utilizing irreversible cysteine cathepsin inhibitor as trapping agent to increase the tumor residence time of receptor-targeted agents. The targeted constructs incorporating these cysteine cathepsin trapping agents were able to form high mol. weight adducts with intracellular cysteine cathepsins, thus achieving superior retention in tumor tissues.

Chemical Communications (Cambridge, United Kingdom) published new progress about 2418-95-3. 2418-95-3 belongs to amides-buliding-blocks, auxiliary class Chiral,Carboxylic acid,Amine,Aliphatic hydrocarbon chain,Ester,Amino acide derivatives, name is H-Lys(Boc)-OH, and the molecular formula is C11H22N2O4, Application In Synthesis of 2418-95-3.

Referemce:
https://en.wikipedia.org/wiki/Amide,
Amide – an overview | ScienceDirect Topics

Wu, Yueming published the artcileLithium hexamethyldisilazide initiated superfast ring opening polymerization of alpha-amino acid N-carboxyanhydrides, Application of H-Lys(Boc)-OH, the publication is Nature Communications (2018), 9(1), 5297, database is CAplus and MEDLINE.

Polypeptides have broad applications and can be prepared via ring-opening polymerization of α-amino acid N-carboxyanhydrides (NCAs). Conventional initiators, such as primary amines, give slow NCA polymerization, which requires multiple days to reach completion and can result in substantial side reactions, especially for very reactive NCAs. Moreover, current NCA polymerizations are very sensitive to moisture and must typically be conducted in a glove box. Here we show that lithium hexamethyldisilazide (LiHMDS) initiates an extremely rapid NCA polymerization process that is completed within minutes or hours and can be conducted in an open vessel. Polypeptides with variable chain length (DP = 20-1294) and narrow mol. weight distribution (Mw/Mn = 1.08-1.28) were readily prepared with this approach. Mechanistic studies support an anionic ring opening polymerization mechanism. This living NCA polymerization method allowed rapid synthesis of polypeptide libraries for high-throughput functional screening.

Nature Communications published new progress about 2418-95-3. 2418-95-3 belongs to amides-buliding-blocks, auxiliary class Chiral,Carboxylic acid,Amine,Aliphatic hydrocarbon chain,Ester,Amino acide derivatives, name is H-Lys(Boc)-OH, and the molecular formula is C10H18O, Application of H-Lys(Boc)-OH.

Referemce:
https://en.wikipedia.org/wiki/Amide,
Amide – an overview | ScienceDirect Topics

Bi, Xiaobao published the artcileImmobilization and Intracellular Delivery of Circular Proteins by Modifying a Genetically Incorporated Unnatural Amino Acid, Formula: C11H22N2O4, the publication is Bioconjugate Chemistry (2018), 29(7), 2170-2175, database is CAplus and MEDLINE.

Backbone-cyclic proteins are of great scientific and therapeutic interest owing to their higher stability over their linear counterparts. Modification of such cyclic proteins at a selected site would further enhance their versatility. Here we report a chemoenzymic strategy to engineer site-selectively modified cyclic proteins by combining butelase-mediated macrocyclization with the genetic code expansion methodol. Using this strategy, we prepared a cyclic protein which was modified with biotin or a cell-penetrating peptide at a genetically incorporated noncanonical amino acid, making the cyclization-stabilized protein further amenable for site-specific immobilization and intracellular delivery. Our results point to a new avenue to engineering novel cyclic proteins with improved physicochem. and pharmacol. properties for potential applications in biotechnol. and medicine.

Bioconjugate Chemistry published new progress about 2418-95-3. 2418-95-3 belongs to amides-buliding-blocks, auxiliary class Chiral,Carboxylic acid,Amine,Aliphatic hydrocarbon chain,Ester,Amino acide derivatives, name is H-Lys(Boc)-OH, and the molecular formula is C11H22N2O4, Formula: C11H22N2O4.

Referemce:
https://en.wikipedia.org/wiki/Amide,
Amide – an overview | ScienceDirect Topics

Hattori, Tomohiro published the artcileSynthesis of silacyclic dipeptides: Peptide elongation at both N- and C-termini of dipeptide, Related Products of amides-buliding-blocks, the publication is Journal of the American Chemical Society (2022), 144(4), 1758-1765, database is CAplus and MEDLINE.

A new type of peptide bond formation utilizing silacyclic amino acids or peptides is described. This work has the following advantages: (1) imidazolylsilane is a highly fascinating coupling reagent for dipeptide synthesis from N-,C-terminal unprotected amino acids with amino acid tert-Bu esters; (2) deprotection of the tert-Bu ester at the C-terminus and cyclization sequentially proceed depending on reaction conditions to afford novel silacyclic dipeptides; (3) the cyclized products show a remarkable capacity as substrates of peptide elongation because the silacyclic compounds can act as both nucleophiles and electrophiles, and this capacity lead to one-pot site-selective tetra- and oligopeptide syntheses. These innovative advantages will help to simplify classical peptide synthesis significantly.

Journal of the American Chemical Society published new progress about 2418-95-3. 2418-95-3 belongs to amides-buliding-blocks, auxiliary class Chiral,Carboxylic acid,Amine,Aliphatic hydrocarbon chain,Ester,Amino acide derivatives, name is H-Lys(Boc)-OH, and the molecular formula is C11H22N2O4, Related Products of amides-buliding-blocks.

Referemce:
https://en.wikipedia.org/wiki/Amide,
Amide – an overview | ScienceDirect Topics

Muramatsu, Wataru published the artcilePeptide bond formation of amino acids by transient masking with silylating reagents, Recommanded Product: H-Lys(Boc)-OH, the publication is Journal of the American Chemical Society (2021), 143(18), 6792-6797, database is CAplus and MEDLINE.

A one-pot peptide bond-forming reaction has been developed using unprotected amino acids and peptides. Two different silylating reagents, HSi[OCH(CF₃)₂]₃ and MTBSTFA, are instrumental for the successful implementation of this approach, being used for the activation and transient masking of unprotected amino acids and peptides at C-termini and N-termini, resp. Furthermore, CsF and imidazole are used as catalysts, activating HSi[OCH(CF₃)₂]₃ and also accelerating chemoselective silylation. This method is versatile as it tolerates side chains that bear a range of functional groups, while providing up to >99% yields of corresponding peptides without any racemization or polymerization

Journal of the American Chemical Society published new progress about 2418-95-3. 2418-95-3 belongs to amides-buliding-blocks, auxiliary class Chiral,Carboxylic acid,Amine,Aliphatic hydrocarbon chain,Ester,Amino acide derivatives, name is H-Lys(Boc)-OH, and the molecular formula is C11H22N2O4, Recommanded Product: H-Lys(Boc)-OH.

Referemce:
https://en.wikipedia.org/wiki/Amide,
Amide – an overview | ScienceDirect Topics

Seki, Eiko published the artcileFully productive cell-free genetic code expansion by structure-based engineering of Methanomethylophilus alvus pyrrolysyl-tRNA synthetase, Category: amides-buliding-blocks, the publication is ACS Synthetic Biology (2020), 9(4), 718-732, database is CAplus and MEDLINE.

Pyrrolysyl-tRNA synthetase (PylRS)/tRNA^Pyl pairs from Methanosarcina mazei and Methanosarcina barkeri are widely used for site-specific incorporations of non-canonical amino acids into proteins (genetic code expansion). In this study, we achieved the full productivity of cell-free protein synthesis for difficult, bulky non-canonical amino acids, such as N^ε-((((E)-cyclooct-2-en-1-yl)oxy)carbonyl)-L-lysine (TCO*Lys), by using Methanomethylophilus alvus PylRS. First, based on the crystal structure of M. alvus PylRS, the productivities for various non-canonical amino acids were greatly increased by rational engineering of the amino acid-binding pocket. The productivities were further enhanced by using a much higher concentration of PylRS over that of M. mazei PylRS, or by mutating the outer layer of the amino acid-binding pocket. Thus, we achieved full productivity even for TCO*Lys. The quantity and quality of the cell-free-produced antibody fragment containing TCO*Lys were drastically improved. These results demonstrate the importance of full productivity for the expanded genetic code.

ACS Synthetic Biology published new progress about 2418-95-3. 2418-95-3 belongs to amides-buliding-blocks, auxiliary class Chiral,Carboxylic acid,Amine,Aliphatic hydrocarbon chain,Ester,Amino acide derivatives, name is H-Lys(Boc)-OH, and the molecular formula is C17H29BO2, Category: amides-buliding-blocks.

Referemce:
https://en.wikipedia.org/wiki/Amide,
Amide – an overview | ScienceDirect Topics