Journal
NATURE PROTOCOLS
Volume 1, Issue 5, Pages 2377-2385Publisher
NATURE PUBLISHING GROUP
DOI: 10.1038/nprot.2006.319
Keywords
-
Categories
Funding
- NATIONAL CANCER INSTITUTE [R01CA112314] Funding Source: NIH RePORTER
- NCI NIH HHS [1R01CA112314-01A1] Funding Source: Medline
Ask authors/readers for more resources
The sialic acid biosynthetic pathway in mammalian cells utilizes N-acetyl-D-mannosamine (ManNAc) as a natural metabolic precursor and has the remarkable ability to biosynthetically process non-natural ManNAc analogs. Herein, we describe a recipe-style protocol for the synthesis of the novel peracetylated analog Ac(5)ManNTGc (1) that contains a pendant acetylthio- group and enables incorporation of thiol functionalities into the glycocalyx of living cells. We also describe the synthesis of the oxygen analog Ac(5)ManNGc (2), which serves as an appropriate control compound for biological experiments with 1. Both 1 and 2 were prepared from a reported, common intermediate 8, which is selectively acetylated at the hydroxyl groups. In contrast to previous methods, this synthetic approach introduces O-acetyl groups first, followed by N-acylation. Starting from the commercially available D-mannosamine hydrochloride (5), gram quantities of both 1 and 2 can be prepared over five steps in about 2-3 weeks.
Authors
I am an author on this paper
Click your name to claim this paper and add it to your profile.
Reviews
Recommended
No Data Available