Hydrazone- and hydrazide-containing N-substituted glycines as peptoid surrogates for expedited library synthesis: applications to the preparation of Tsg101-directed HIV-1 budding antagonists

F Liu; A.G. Stephen; Catherine Sarah Adamson; K Gousset; M.J. Aman; E.O. Freed; R.J. Fisher; T.R. Jr Burke

doi:DOI: 10.1021/ol0622211

Hydrazone- and hydrazide-containing N-substituted glycines as peptoid surrogates for expedited library synthesis: applications to the preparation of Tsg101-directed HIV-1 budding antagonists

F Liu, A.G. Stephen, Catherine Sarah Adamson, K Gousset, M.J. Aman, E.O. Freed, R.J. Fisher, T.R. Jr Burke

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

Abstract

Replacing the Pro6 in the p6Gag-derived 9-mer “P-E-P-T-A-P-P-E-E” with N-substituted glycine (NSG) residues is problematic. However, incorporation of hydrazone amides (“peptoid hydrazones”) can be readily achieved in library fashion. Furthermore, reduction of these hydrazones to N-substituted “peptoid hydrazides” affords a facile route to library diversification. This approach is demonstrated by application to Tsg101-binding compounds designed as potential HIV budding antagonists.

Original language	English
Pages (from-to)	5165-5168
Journal	Organic Letters
Volume	8
Issue number	22
DOIs	https://doi.org/DOI: 10.1021/ol0622211
Publication status	Published - Oct 2006

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DOI: 10.1021/ol0622211

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Liu, F., Stephen, A. G., Adamson, C. S., Gousset, K., Aman, M. J., Freed, E. O., Fisher, R. J., & Burke, T. R. J. (2006). Hydrazone- and hydrazide-containing N-substituted glycines as peptoid surrogates for expedited library synthesis: applications to the preparation of Tsg101-directed HIV-1 budding antagonists. Organic Letters, 8(22), 5165-5168. https://doi.org/DOI: 10.1021/ol0622211

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title = "Hydrazone- and hydrazide-containing N-substituted glycines as peptoid surrogates for expedited library synthesis: applications to the preparation of Tsg101-directed HIV-1 budding antagonists",

abstract = "Replacing the Pro6 in the p6Gag-derived 9-mer “P-E-P-T-A-P-P-E-E” with N-substituted glycine (NSG) residues is problematic. However, incorporation of hydrazone amides (“peptoid hydrazones”) can be readily achieved in library fashion. Furthermore, reduction of these hydrazones to N-substituted “peptoid hydrazides” affords a facile route to library diversification. This approach is demonstrated by application to Tsg101-binding compounds designed as potential HIV budding antagonists.",

author = "F Liu and A.G. Stephen and Adamson, {Catherine Sarah} and K Gousset and M.J. Aman and E.O. Freed and R.J. Fisher and Burke, {T.R. Jr}",

year = "2006",

month = oct,

doi = "DOI: 10.1021/ol0622211",

language = "English",

volume = "8",

pages = "5165--5168",

journal = "Organic Letters",

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publisher = "American Chemical Society (ACS)",

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Liu, F, Stephen, AG, Adamson, CS, Gousset, K, Aman, MJ, Freed, EO, Fisher, RJ & Burke, TRJ 2006, 'Hydrazone- and hydrazide-containing N-substituted glycines as peptoid surrogates for expedited library synthesis: applications to the preparation of Tsg101-directed HIV-1 budding antagonists', Organic Letters, vol. 8, no. 22, pp. 5165-5168. https://doi.org/DOI: 10.1021/ol0622211

Hydrazone- and hydrazide-containing N-substituted glycines as peptoid surrogates for expedited library synthesis: applications to the preparation of Tsg101-directed HIV-1 budding antagonists. / Liu, F; Stephen, A.G.; Adamson, Catherine Sarah et al.
In: Organic Letters, Vol. 8, No. 22, 10.2006, p. 5165-5168.

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

TY - JOUR

T1 - Hydrazone- and hydrazide-containing N-substituted glycines as peptoid surrogates for expedited library synthesis: applications to the preparation of Tsg101-directed HIV-1 budding antagonists

AU - Liu, F

AU - Stephen, A.G.

AU - Adamson, Catherine Sarah

AU - Gousset, K

AU - Aman, M.J.

AU - Freed, E.O.

AU - Fisher, R.J.

AU - Burke, T.R. Jr

PY - 2006/10

Y1 - 2006/10

N2 - Replacing the Pro6 in the p6Gag-derived 9-mer “P-E-P-T-A-P-P-E-E” with N-substituted glycine (NSG) residues is problematic. However, incorporation of hydrazone amides (“peptoid hydrazones”) can be readily achieved in library fashion. Furthermore, reduction of these hydrazones to N-substituted “peptoid hydrazides” affords a facile route to library diversification. This approach is demonstrated by application to Tsg101-binding compounds designed as potential HIV budding antagonists.

AB - Replacing the Pro6 in the p6Gag-derived 9-mer “P-E-P-T-A-P-P-E-E” with N-substituted glycine (NSG) residues is problematic. However, incorporation of hydrazone amides (“peptoid hydrazones”) can be readily achieved in library fashion. Furthermore, reduction of these hydrazones to N-substituted “peptoid hydrazides” affords a facile route to library diversification. This approach is demonstrated by application to Tsg101-binding compounds designed as potential HIV budding antagonists.

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UR - http://pubs.acs.org/doi/abs/10.1021/ol0622211

U2 - DOI: 10.1021/ol0622211

DO - DOI: 10.1021/ol0622211

M3 - Article

SN - 1523-7060

VL - 8

SP - 5165

EP - 5168

JO - Organic Letters

JF - Organic Letters

IS - 22

ER -

Hydrazone- and hydrazide-containing N-substituted glycines as peptoid surrogates for expedited library synthesis: applications to the preparation of Tsg101-directed HIV-1 budding antagonists

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