2D green SPPS: green solvents for on-resin removal of acid sensitive protecting groups and lactamization
Aiming at greener synthesis of complex peptides we report that conventional one-dimensional (1D) green solid-phase peptide synthesis (SPPS) is elevated to a two-dimensional (2D) concept in which side chains in peptide resins are functionalized by suitable green tactics. Specifically, we disclose on-...
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Veröffentlicht in: | Green chemistry : an international journal and green chemistry resource : GC 2019-05, Vol.21 (1), p.2594-26 |
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Format: | Artikel |
Sprache: | eng |
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Zusammenfassung: | Aiming at greener synthesis of complex peptides we report that conventional one-dimensional (1D) green solid-phase peptide synthesis (SPPS) is elevated to a two-dimensional (2D) concept in which side chains in peptide resins are functionalized by suitable green tactics. Specifically, we disclose on-resin deblocking using trifluoroacetic acid (TFA)/triisopropylsilane (TIS) in EtOAc/MeCN used in a synthesis of a melanocortin receptor agonist comprising (i) 1D green SPPS (ii) 2D green SPPS by an on-resin TFA/TIS in EtOAc/MeCN deprotection of Lys(Mtt) and Asp(O-2-Ph
i
Pr) followed by a lactamization using PyBOP/DIEA in NBP/EtOAc (iii) TFA cleavage followed by green precipitation using 4-methyltetrahydropyran (MTHP)/
n
-heptane. A further application for our green deprotection protocol was found in peptide fragment cleavages off CTC resins.
An SPPS method for the on-resin removal of acid labile protecting groups using TFA/TIS in EtOAc/MeCN and lactamization with PyBOP/DIEA in NBP/EtOAc is reported. |
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ISSN: | 1463-9262 1463-9270 |
DOI: | 10.1039/c9gc00898e |