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. Author manuscript; available in PMC: 2016 Jun 10.
Published in final edited form as: J Am Chem Soc. 2015 Jun 2;137(22):6987–6990. doi: 10.1021/jacs.5b01607

Table 1.

Generation of Peptidoglycan Derivatives from 2-Amino-MDP (3)

graphic file with name nihms771558u1.jpg
Entry Electrophile Product Yield
1a,b Acetoxyacetic acid NHS ester 8,R=C(O)CH2OAc 48%
2 Methoxyacetic anhydride 9,R = C(O)CH2OMe 78%
3 Ethyl triflouroacetate 10,R=C(O)CF3 92%
4c Succinic anhydride 11,R = C(O)(CH2)2CO2H 66%
5d Levulinic acid NHS ester 12, R = C(O)(CH2)2C(O)Me 77%
6d 2-Azidoacetic acid NHS ester 13,R=C(O)CH2N3 88%
7c,e Dansyl chloride 14, R= Dansyl 48%
8 Biotin NHS ester 15, R = Biotin 79%
a

Electrophile prepared according to literature precedent.15

b

Per-formed in H2O with NaHCO3.

c

Stirred 24 h.

d

Electrophile prepared with EDC/NHS.

e

Performed in H2O/DMF.