Organoboron catalysis for direct amide/peptide bond formation DOI Creative Commons
Masayoshi Koshizuka, Naoya Takahashi, Naoyuki Shimada

et al.

Chemical Communications, Journal Year: 2024, Volume and Issue: 60(80), P. 11202 - 11222

Published: Jan. 1, 2024

This review explores studies on the development of direct dehydrative amide/peptide bond formation from carboxylic acids using organoboron catalysis.

Language: Английский

Process Mass Intensity (PMI): A Holistic Analysis of Current Peptide Manufacturing Processes Informs Sustainability in Peptide Synthesis DOI Creative Commons
Ivy Kekessie, Katarzyna Wegner, Isamir Martinez

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(7), P. 4261 - 4282

Published: March 20, 2024

Small molecule therapeutics represent the majority of FDA-approved drugs. Yet, many attractive targets are poorly tractable by small molecules, generating a need for new therapeutic modalities. Due to their biocompatibility profile and structural versatility, peptide-based possible solution. Additionally, in past two decades, advances peptide design, delivery, formulation, devices have occurred, making peptides an modality. However, manufacturing is often limited solid-phase synthesis (SPPS), liquid phase (LPPS), lesser extent hybrid SPPS/LPPS, with SPPS emerging as predominant platform technology synthesis. involves use excess solvents reagents which negatively impact environment, thus highlighting newer technologies reduce environmental footprint. Herein, fourteen American Chemical Society Green Chemistry Institute Pharmaceutical Roundtable (ACS GCIPR) member companies portfolio compiled Process Mass Intensity (PMI) metrics help inform sustainability efforts This includes PMI assessment on 40 synthetic processes at various development stages pharma, classified according phase. most comprehensive date. The process was divided into (synthesis, purification, isolation) determine respective PMI. On average, (SPPS) (PMI ≈ 13,000) does not compare favorably other modalities such molecules median 168–308) biopharmaceuticals 8300). Thus, high warrants more environmentally friendly manufacturing.

Language: Английский

Citations

33

Identifying general reaction conditions by bandit optimization DOI
Jason Y. Wang, Jason M. Stevens, Stavros K. Kariofillis

et al.

Nature, Journal Year: 2024, Volume and Issue: 626(8001), P. 1025 - 1033

Published: Feb. 28, 2024

Language: Английский

Citations

21

AJICAP Second Generation: Improved Chemical Site-Specific Conjugation Technology for Antibody–Drug Conjugate Production DOI Creative Commons

Tomohiro Fujii,

Yutaka Matsuda,

Takuya Seki

et al.

Bioconjugate Chemistry, Journal Year: 2023, Volume and Issue: unknown

Published: March 9, 2023

The site-directed chemical conjugation of antibodies remains an area great interest and active efforts within the antibody-drug conjugate (ADC) community. We previously reported a unique site modification using class immunoglobulin-G (IgG) Fc-affinity reagents to establish versatile, streamlined, site-selective native enhance therapeutic index resultant ADCs. This methodology, termed "AJICAP", successfully modified Lys248 produce site-specific ADC with wider than Food Drug Administration-approved ADC, Kadcyla. However, long reaction sequences, including reduction-oxidation (redox) treatment, increased aggregation level. In this manuscript, we aimed present updated Fc-affinity-mediated technology named "AJICAP second generation" without redox treatment utilizing "one-pot" antibody reaction. stability Fc affinity was improved owing structural optimization, enabling production various ADCs aggregation. addition conjugation, Lys288 conjugated homogeneous drug-to-antibody ratio 2 were produced different peptide reagent possessing proper spacer linkage. These two technologies used over 20 from several combinations drug linkers. in vivo profile also compared. Furthermore, nontraditional production, such as antibody-protein conjugates antibody-oligonucleotide conjugates, achieved. results strongly indicate that approach is promising strategy for manufacturing engineering.

Language: Английский

Citations

44

Direct Catalytic Amidations from Carboxylic Acid and Ester Derivatives: A Review DOI Open Access

Armand Taussat,

Renata Marcia de Figueiredo, Jean‐Marc Campagne

et al.

Catalysts, Journal Year: 2023, Volume and Issue: 13(2), P. 366 - 366

Published: Feb. 7, 2023

The prevalence of amides in biological systems and chemical fields such as polymers, materials natural products drives continuous research on novel procedures to obtain these ubiquitous functional groups. Currently, efforts this purpose are mainly focused around the discovery direct catalytic methods that more atom economic, safe practical for diversified applications (e.g., organic, medicinal peptide chemistries, material polymer purposes, etc.), accordance with green chemistry principles. field amide synthesis has attained a level significance number reviews articles addressing it grown exponentially last decade. Rather than providing general overview amidation methods, which have been described broadly well recent literature, review is highlight formation bonds from amines carboxylic acids or esters. goal emphasize mechanistic aspects, but also discuss substrate tolerance racemization issues (when applicable).

Language: Английский

Citations

35

Decarboxylative, Radical C–C Bond Formation with Alkyl or Aryl Carboxylic Acids: Recent Advances DOI Creative Commons
Joshua D. Tibbetts, Alexander J. Cresswell,

Hannah E. Askey

et al.

Synthesis, Journal Year: 2023, Volume and Issue: 55(20), P. 3239 - 3250

Published: April 26, 2023

Abstract The ubiquity of carboxylic acids as naturally derived or man-made chemical feedstocks has spurred the development powerful, decarboxylative C–C bond-forming transformations for organic synthesis. Carboxylic benefit not only from extensive commercial availability, but are stable surrogates organohalides organometallic reagents in transition-metal-catalysed cross-coupling. Open shell reactivity (or derivatives thereof) to furnish carbon-centred radicals is proving transformative synthetic chemistry, enabling novel and strategy-level C(sp3)–C bond disconnections with exquisite chemoselectivity. This short review will summarise several latest advances this ever-expanding area. 1 Introduction 2 Improved Decarboxylative Arylations 3 sp3–sp3 Cross-Coupling Acids Aliphatic Bromides 4 Alcohols Amines 5 Doubly 6 Bond Formation (Hetero)aryl 7 Conclusions

Language: Английский

Citations

28

Direct formation of amide/peptide bonds from carboxylic acids: no traditional coupling reagents, 1-pot, and green DOI Creative Commons
Kaitlyn M. Freiberg,

Rahul D. Kavthe,

Rohan M. Thomas

et al.

Chemical Science, Journal Year: 2023, Volume and Issue: 14(13), P. 3462 - 3469

Published: Jan. 1, 2023

Technology for generating especially important amide and peptide bonds from carboxylic acids amines that avoids traditional coupling reagents is described. The 1-pot processes developed rely on thioester formation, neat, using a simple dithiocarbamate, are safe green, Nature-inspired thioesters then converted to the targeted functionality.

Language: Английский

Citations

24

Conformal Fixation Strategies and Bioadhesives for Soft Bioelectronics DOI
Jaejin Park, Hyun Woo Kim, Selin Lim

et al.

Advanced Functional Materials, Journal Year: 2024, Volume and Issue: 34(22)

Published: Jan. 6, 2024

Abstract Flexible wearable and implantable devices are contributing to the healthcare field by enabling intuitive interfaces with tissues of human body through their thin form factors, which enable more accurate monitoring signals effective delivery therapy. The development such is accompanied an increasing interest in strategies technologies for conformally fixing adhering flexible biomedical place acquire high‐quality biosignals over a long period, even subtle movements target. Owing various mechanical properties wet or dynamic environments tissues, it necessary use different adhesion that consider biocompatibility cohesive each case. This paper provides in‐depth analysis recent bio‐adhesives practical applications classifying them into: 1) Conventional Fixation, 2) Mechanical 3) Chemical Adhesion, based on mechanism, 4) Functional Adhesion 5) Biomimetic unique properties. Furthermore, principles detailed mechanisms strategy design characteristics bioadhesives thoroughly reviewed provide valuable insights overall summary prospects challenges future technology.

Language: Английский

Citations

16

Amidation by reactive extrusion for the synthesis of active pharmaceutical ingredients teriflunomide and moclobemide DOI Creative Commons
Matthieu Lavayssiere, Frédéric Lamaty

Chemical Communications, Journal Year: 2023, Volume and Issue: 59(23), P. 3439 - 3442

Published: Jan. 1, 2023

The solventless synthesis of an amide was performed in a twin-screw extruder the presence coupling agent, providing high yielding and productive method. reaction conditions were optimized to prepare APIs, teriflunomide moclobemide.

Language: Английский

Citations

20

Crosslinking Methods in Polysaccharide-Based Hydrogels for Drug Delivery Systems DOI Open Access

Mayara Thamela Pessoa Paiva,

João Otávio Ferraro Kishima, Jaquellyne Bittencourt Moraes Duarte da Silva

et al.

Deleted Journal, Journal Year: 2023, Volume and Issue: 2(1), P. 288 - 306

Published: July 26, 2023

Polysaccharides are inspiring and valuable molecules to the development of novel drug delivery systems owing their natural availability, non-toxicity, biocompatibility, good biological performance, chemical similarity physiological environment, besides noticeable use for tailored-materials assembly. Biodegradable hydrogels based on polysaccharides have been widely studied as potential pharmaceutical forms due controlled release properties, which improve bioavailability, therapeutic efficacy, patient compliance. Despite these advantages, polysaccharide materials present insufficient mechanical properties or processability, thus, overcome drawbacks, feasible suitable crosslinking methods employed strength stability. Therefore, this review presents recent advances in hydrogels, including chitosan, cellulose, hyaluronic acid, alginate, providing examples manufacturing processes with emphasis carriers delivery. Polysaccharide-based represent a sustainable, biocompatible, appreciable alternative obtain systems.

Language: Английский

Citations

20

Visible-Light-Promoted α-C(sp3)–H Amidation of Cyclic Ethers under Redox-Neutral Conditions DOI
Shuangqing Li, Xiufang Xu, Jianhui Chen

et al.

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: March 16, 2025

Reported herein is a visible-light-promoted strategy for the α-C(sp3)–H amidation of cyclic ethers using N-acyloxyamide as an oxidative amidating reagent. This transformation provides straightforward approach to various α-amidated under metal- and additive-free conditions. The synthetic utility products was demonstrated through facile transformations, including reduction, allylation, acylation, sulfonamidation, gram-scale reactions. Preliminary mechanistic studies suggest radical/radical cross-coupling process, with C(sp3)–H bond cleavage identified rate-determining step.

Language: Английский

Citations

1