Harnessing the power of a photoinitiated thiol–ene “click” reaction for the efficient synthesis of S-lipidated collagen model peptide amphiphiles

Literature Information

Publication Date 2023-10-05
DOI 10.1039/D3OB01469J
Impact Factor 3.876
Authors

Sujay Prabakar, Wenkai Zhang


View Original

Abstract

A photoinitiated thiol–ene “click” reaction was used to synthesize S-lipidated collagen model peptide amphiphiles. Use of 2-iminothiolane provided an epimerization-free thiol handle required for thiol–ene based incorporation of lipid moieties onto collagen-based peptide sequences. This approach not only led to improvements in the triple helical characteristics of the resulting collagen model peptides but also increased the aqueous solubility of the peptide amphiphiles. As a result, this methodology holds significant potential for the design and advancement of functional peptide amphiphiles, offering enhanced capabilities across a wide range of applications.

Related Literature

Intramolecular charge transfer with N-benzoylaminonaphthalenes. 1-Aminonaphthaleneversus2-aminonaphthalene as electron donors

Xuan Zhang, Chun-Hua Liu, Li-Hong Liu, Lin Guo, Chao-Jie Wang, Yun-Bao Jiang

2003-01-29 Paper

DOI: 10.1039/B210106H

Characterization of binary solvent mixtures: the water–acetonitrile mixture

Francisco García-Blanco

2003-01-06 Paper

DOI: 10.1039/B210405A

DNA recognition by the anthracycline antibiotic respinomycin D: NMR structure of the intercalation complex with d(AGACGTCT)2

Mark S. Searle, Allister J. Maynard, Huw E. L. Williams

2002-12-05 Paper

DOI: 10.1039/B208622K

Synthesis and Suzuki–Miyaura cross coupling reactions for post-synthetic modification of a tetrabromo-anthracenyl porphyrin

Joffrey Pijeat, Yannick J. Dappe, Pierre Thuéry, Stéphane Campidelli

2018-10-09 Paper

DOI: 10.1039/C8OB02150C

Tuning the keto equilibrium in 4-substituted dipicolinic acid derivatives

Anne-Sophie Chauvin, Sandrine Gras, Jean-Claude G. Bünzli

2003-01-22 Paper

DOI: 10.1039/B211267C

Bioactive polycyclic polyprenylated acylphloroglucinols from Hypericum perforatum

Yi Guo, Na Zhang, Weiguang Sun, Xueyan Duan, Qing Zhang, Qun Zhou, Chunmei Chen, Hucheng Zhu, Zengwei Luo, Junjun Liu, Xiao-Nian Li, Yongbo Xue, Yonghui Zhang

2018-10-08 Paper

DOI: 10.1039/C8OB02067A

Studies toward the synthesis of strevertenes A and G: stereoselective construction of C1–C19 segments of the molecules

Tapan Kumar Kuilya, Subhendu Das, Dhiman Saha, Rajib Kumar Goswami

2018-08-23 Paper

DOI: 10.1039/C8OB01754A

Palladium-catalyzed cascade carboesterification of norbornene with alkynes

Can Li, Jianxiao Li, Huanfeng Jiang

2018-08-29 Paper

DOI: 10.1039/C8OB01799A

You might also like

Compound Q&A

How should 2-Methylbenzene-1,4-diamine dihydrochloride (CAS: 615-45-2) be stored?

2-Methylbenzene-1,4-diamine dihydrochloride (CAS: 615-45-2) should be stored in ...

615-45-22-Methylbenzene-1,4-...
Compound Q&A

Is (1S,4S)-2,5-Diazabicyclo[2.2.1]heptane dihydrobromide (CAS: 132747-20-7) safe?

(1S,4S)-2,5-Diazabicyclo[2.2.1]heptane dihydrobromide is generally considered sa...

132747-20-7(1S,4S)-2,5-Diazabic...
Compound Q&A

What industries use (6-Chloropyridazin-3-YL)methanamine (CAS: 871826-15-2)?

(6-Chloropyridazin-3-YL)methanamine finds applications in the pharmaceutical ind...

871826-15-2(6-Chloropyridazin-3...
Compound Q&A

What are the main uses of 2-Fluoro-3-methylphenol (CAS: 77772-72-6)?

2-Fluoro-3-methylphenol is primarily used in the synthesis of pharmaceuticals, p...

77772-72-62-Fluoro-3-methylphe...
Compound Q&A

What precautions should be taken when handling 3-Methoxy-4-nitrobenzonitrile (CAS: 177476-75-4)?

When handling 3-Methoxy-4-nitrobenzonitrile, it is important to wear appropriate...

177476-75-43-Methoxy-4-nitroben...
Compound Q&A

What precautions should be taken when handling 1,3-Oxazolo[4,5-b]pyridine-2(3H)-thione (CAS: 211949-57-4)?

When handling 1,3-Oxazolo[4,5-b]pyridine-2(3H)-thione (CAS: 211949-57-4), it is ...

211949-57-4[1,3]Oxazolo[4,5-b]p...
Compound Q&A

What regulatory guidelines apply to 4-Ethynylbenzamide (CAS: 90347-86-7)?

4-Ethynylbenzamide (CAS: 90347-86-7) falls under various regulatory guidelines i...

90347-86-74-Ethynylbenzamide
Compound Q&A

What are the main uses of 3-(2-Ethylphenyl)-2-thioxo-4-imidazolidinone (CAS: 186822-57-1)?

3-(2-Ethylphenyl)-2-thioxo-4-imidazolidinone is primarily used as an intermediat...

186822-57-13-(2-Ethylphenyl)-2-...
Compound Q&A

What is (2-Fluoro-6-methoxyphenyl)acetic acid (CAS: 500912-19-6)?

(2-Fluoro-6-methoxyphenyl)acetic acid, also known as 4-fluoro-3-methoxybenzoic a...

500912-19-6(2-Fluoro-6-methoxyp...
Compound Q&A

What is the market or research trend for 2-[4-(Hydroxymethyl)phenoxy]ethanol (CAS: 102196-18-9)?

Market trends for 2-[4-(Hydroxymethyl)phenoxy]ethanol (CAS: 102196-18-9) indicat...

102196-18-92-[4-(Hydroxymethyl)...

Source Journal

Organic & Biomolecular Chemistry

Organic & Biomolecular Chemistry
CiteScore: 3.4
Self-citation Rate: 10.3%
Articles per Year: 1041

Organic & Biomolecular Chemistry (OBC) publishes original and high impact research and reviews in organic chemistry. We welcome research that shows new or significantly improved protocols or methodologies in total synthesis, synthetic methodology or physical and theoretical organic chemistry as well as research that shows a significant advance in the organic chemistry or molecular design aspects of chemical biology, catalysis, supramolecular and macromolecular chemistry, theoretical chemistry, mechanism-oriented physical organic chemistry, medicinal chemistry or natural products. Articles published in the journal should report new work which makes a highly-significant impact in the field. Routine and incremental work is generally not suitable for publication in the journal. More details about key areas of our scope are below. In all cases authors should include in their article clear rationale for why their research has been carried out.

Recommended Suppliers

Disclaimer
This page provides academic journal information for reference and research purposes only. We are not affiliated with any journal publishers and do not handle publication submissions. For publication-related inquiries, please contact the respective journal publishers directly.
If you notice any inaccuracies in the information displayed, please contact us at support@chemtradehub.com. We will promptly review and address your concerns.