215056-52-3

Upstream product

• 1694-92-4 2-Nitrobenzenesulfonyl chloride 
• 84508-21-4 glycine methyl ester protonated form 
• 141381-72-8 1H-benzo[d][1,2,3]triazol-1-yl 2-nitrobenzenesulfonate 
• 616-34-2 methoxycarbonylmethylamine 
• 5680-79-5 glycine ethyl ester hydrochloride 
• 186581-53-3 diazomethane 
• 15054-42-9 2-[(2-nitrobenzene)sulfonamido]acetic acid 
• 1441409-96-6 (E)-ethyl 2-cyano-2-(2-nitrophenylsulfonyloxyimino)acetate 

Downstream Products

• 215056-58-9 [(2-tert-butoxycarbonylamino-ethyl)-(2-nitro-benzenesulfonyl)-amino]-acetic acid methyl ester 
• 1026671-50-0 [allyl-(2-nitro-benzenesulfonyl)-amino]-acetic acid methyl ester 
• 937203-88-8 C₂₁H₃₄N₂O₇SiS 
• 1360804-50-7 C₂₅H₂₅ClN₆O₁₃S 
• 1360804-52-9 C₂₅H₂₅ClN₆O₁₃S 
• 501097-08-1 [(3-tert-butoxycarbonylamino-propyl)-(2-nitro-benzenesulfonyl)-amino]-acetic acid methyl ester 
• 380228-29-5 [(2-tert-butoxycarbonylamino-3-methyl-butyl)-(2-nitro-benzenesulfonyl)-amino]-acetic acid methyl ester 
• 380228-30-8 [(2-tert-butoxycarbonylamino-4-methyl-pentyl)-(2-nitro-benzenesulfonyl)-amino]-acetic acid methyl ester 
• 380228-31-9 [(2-tert-butoxycarbonylamino-3-phenyl-propyl)-(2-nitro-benzenesulfonyl)-amino]-acetic acid methyl ester 
• 380228-28-4 [(2-tert-butoxycarbonylamino-propyl)-(2-nitro-benzenesulfonyl)-amino]-acetic acid methyl ester 

Relevant academic research and scientific papers

Conformational modulation of peptides using β-amino benzenesulfonic acid (SAnt)

This communication describes the utility of a conformationally restricted aromatic β-amino acid (2-aminobenzenesulfonic acid, SAnt) inducing various folding interactions in short peptides. Sandwiching SAnt between diverse amino acid residues was shown to form robust folded architectures featuring a variety of H-bonded networks, suggesting its utility in inducing peptide folding. This journal is

Trimodular Solution-Phase Protocol for Rapid Large-Scale Synthesis of Hydrogen Bond Surrogate-Constrained α-Helicomimics

Scalability, optimal reagent usage, high yields, easy isolation, and cost-effectiveness, are key for the applicability of synthetic methodologies in the production of potential therapeutics. Hydrogen bond surrogate (HBS) constrained α-helical peptides (α-helicomimics) have shown promise as therapeutics based on their efficiency to interfere with protein-biomolecular interactions. The propyl HBS-constrained α-helicomimics have shown the highest helicities in both single turn and extended, α-helices (STαH, EαH). Here we present a solution-phase synthetic (SPS) method, for the rapid, large-scale, low-cost synthesis of libraries of STαH and EαH in high yields. The key to efficiency is our trimodular (M1, M2, M3) synthetic protocol where M1 is a library of HBS-linked peptidomimetic synthons of both STαH and EαH; M2 and M3 are desired oligopeptide libraries. Advantages of the trimodular method over conventional unimodular methods are demonstrated through the synthesis of large-scale libraries of M1, STαH, and EαH.

Rhodium-Catalyzed Enantioselective Synthesis of Oxazinones via an Asymmetric Ring Opening-Lactonization Cascade of Oxabicyclic Alkenes

The rhodium-catalyzed asymmetric ring opening reaction of oxabicyclic alkenes is shown to be an efficient method for synthesizing chiral heterocycles. We demonstrate that the pairwise combination of chiral catalyst with chiral amino-acid-derived pronucleophiles results in a stereodivergent synthesis of diastereomeric hydroxyesters. A favorable conformational preference induces the subsequent lactonization of one diastereomer leading to the highly enantioselective synthesis of oxazinones.

Hydrogen bond surrogate stabilized water soluble 310-helix from a disordered pentapeptide containing coded α-amino acids

Replacing a hypothetical i + 3 → i peptide H-bond in a disordered pentapeptide, that lacks any helicogenic Cα-tetrasubstituted residues, with a propyl linker and carbamylating the N-terminal nitrogen constrains it in the elusive 310-helical structure with high helicity and stability under varying conditions of temperature and pH, confirmed by NMR and CD analyses.

Methyl 2-(Bromomethyl)acrylate, Methyl Acrylate, and Glycine in the Synthesis of Functionalized Pyrrolidones

Possible application of methyl 2-(bromomethyl)acrylate, methyl acrylate, and glycine in the synthesis of functionalized pyrrolidones was considered.

PEPTIDE NUCLEIC ACID MONOMER AND A PREPARATION METHOD

The disclosure in various embodiments is related to a peptide nucleic acid monomer (VI) and an improved process for preparation of PNA (VI) using nosyl-group containing starting material. The process includes reacting amino acid with a nosyl group. The nosyl protected amino acid is alkylated with 2-(Boc-amino)ethyl bromide to obtain an intermediate. The nosyl group of the obtained intermediate is removed to form a PNA backbone. The PNA backbone upon addition of a modified nucleobase results in the formation of a PNA monomer (VI). The obtained PNA monomer exhibits either chiral or achiral geometric properties.

Design and Synthesis of a Novel N-(1H-tetrazol-5-yl)methyl Cyclic Peptoid Using Nosyl-protected N-(1-trityl-1H-tetrazol-5-yl)methyl Substituted Glycine

Abstract: A solid phase synthesis of a cyclic peptoid bearing (1H-tetrazol-5-yl)methyl as N-substituent has been developed employing the monomer approach. The requisite monomeric Nosyl-protected N-(1-trityl-1H-tetrazol-5-yl)methyl substituted glycine was

Sulfonamide synthesis via oxyma-O-sulfonates - Compatibility to acid sensitive groups and solid-phase peptide synthesis

A milder and more efficient procedure for the synthesis of sulfonamides by activating sulfonic acid groups as the corresponding sulfonate esters of ethyl 2-cyano-2-(hydroxyimino)acetate (Oxyma) is reported. This method is greener than all other existing protocols for the purpose. Other important advantages lie in (a) its applicability to less nucleophilic anilines under ambient and milder conditions and (b) its compatibility with solid phase peptide synthesis and acid-labile groups such as trityl (Trt) and tBu, which empowers the solid phase synthesis of sulfonamides of various peptides. To illustrate this, the syntheses of three sulfonamide derivatives of the peptide GAILG-NH2, which is relevant in the context of drug design against type 2 diabetes, are demonstrated by using Fmoc-based solid-phase peptide synthesis (SPPS). The activation of sulfonic acids as their corresponding O-sulfonate esters facilitates sulfonamide synthesis, which can be applied to those substrates that possess acid-labile functional groups and is compatible with solid phase synthesis. Copyright

Sulfonamide synthesis using N-hydroxybenzotriazole sulfonate: An alternative to pentafluorophenyl (PFP) and trichlorophenyl (TCP) esters of sulfonic acids

The N-hydroxybenzotriazole (HOBt) sulfonate esters undergo amidation under ambient conditions in the presence of di-isopropylethyl amine. This method can be applied to varieties of amines including sterically hindered amino acid esters in less time with reasonably good yields. HOBt ester of sulfonic acids can be a replacement for pentafluorophenyl and trichlorophenyl ester as well as chloride moiety of sulfonyl chloride for amidation.

Total synthesis of (-)-kainic acid via intramolecular michael addition: A second-generation route

A total synthesis of (-)-kainic acid starting from the commercially available 2-azetidinone is described. The key δ-lactone intermediate was concisely prepared from the commercially available azetidinone through the Reformatsky-type reaction and an introduction of a glycine moiety. The construction of the functionalized pyrrolidine ring was executed by a one-pot sequential elimination-Michael addition protocol of a β-amino-δ- lactone intermediate with high diastereoselectivity.