Multipurpose isothiocyanyl alanine/lysine: Use as solvatochromic IR probes and in site specific labeling/ligation of short peptides

Subhendu Sekhar Bag; Suranjan De

doi:10.1016/j.bmcl.2018.02.021

Multipurpose isothiocyanyl alanine/lysine: Use as solvatochromic IR probes and in site specific labeling/ligation of short peptides

Subhendu Sekhar Bag, Suranjan De

Research output: Contribution to journal › Article › peer-review

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Abstract

The solvatochromic IR responsivity of small side chain –NCS in two unexplored unnatural amino acids, isothiocyanyl alanine (^NCSAla = Ita) and lysine (^NCSLys = Itl), without perturbing the conformation is demonstrated in two designed short tripeptide (BocAla-^NCSAla-Ala-OMe) and hexapeptide (BocLeu-Val-Phe-Phe-^NCSLys-Gly-OMe). Demonstration of site specific fluorescent labeling in both the peptides and ligation type reaction in ^NCSLys indicates the novelty of these two amino acids as alternative to the available canonical amino acids.

Original language	English
Pages (from-to)	1404-1409
Number of pages	6
Journal	Bioorganic and Medicinal Chemistry Letters
DOIs	https://doi.org/10.1016/j.bmcl.2018.02.021
State	Published - 1 May 2018
Externally published	Yes

Bibliographical note

Funding Information:
The authors thank the Department of Biotechnology (DBT: BT/PR16620/NER/95/223/2015), New Delhi, Govt. of India for generous funding. S.D. thanks the IIT Guwahati for a fellowship. The CIF, IITG is gratefully acknowledged for 600 MHz NMR facility.

Funding Information:
The authors thank the Department of Biotechnology (DBT: BT/PR16620/NER/95/223/2015), New Delhi, Govt. of India for generous funding. S.D. thanks the IIT Guwahati for a fellowship. The CIF, IITG is gratefully acknowledged for 600 MHz NMR facility.

Publisher Copyright:
© 2018

Keywords

IR sensitive probe
Isothiocyanyl alanine
Isothiocyanyl lysine
Peptide ligation
Site specific labeling

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10.1016/j.bmcl.2018.02.021

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title = "Multipurpose isothiocyanyl alanine/lysine: Use as solvatochromic IR probes and in site specific labeling/ligation of short peptides",

abstract = "The solvatochromic IR responsivity of small side chain –NCS in two unexplored unnatural amino acids, isothiocyanyl alanine (NCSAla = Ita) and lysine (NCSLys = Itl), without perturbing the conformation is demonstrated in two designed short tripeptide (BocAla-NCSAla-Ala-OMe) and hexapeptide (BocLeu-Val-Phe-Phe-NCSLys-Gly-OMe). Demonstration of site specific fluorescent labeling in both the peptides and ligation type reaction in NCSLys indicates the novelty of these two amino acids as alternative to the available canonical amino acids.",

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doi = "10.1016/j.bmcl.2018.02.021",

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Multipurpose isothiocyanyl alanine/lysine: Use as solvatochromic IR probes and in site specific labeling/ligation of short peptides

Abstract

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