206
39. Avery OT, Goebel WF (1929) Chemo-immunological studies on conjugated carbohydrateproteins. II Immunological specificity of synthetic sugar-protein antigens. J Exp Med
50:533–550
40. Pollard AJ, Perrett KP, Beverley PC (2009) Maintaining protection against invasive bacteria
with protein-polysaccharide conjugate vaccines. Nat Rev 9:213–220
41. Daum RS, Hogerman D, Rennels MB, Bewley K, Malinoski F, Rothstein E, Reisinger K,
Block S, Keyserling H, Steinhoff M (1997) Infant immunization with pneumococcal CRM 197
vaccines: effect of saccharide size on immunogenicity and interactions with simultaneously
administrated vaccines. J Infect Dis 176:445–455
42. Lefeber DJ, Kamerling JP, Vliegenthart JFG (2001) Synthesis of Streptococcus pneumoniae
type 3 neoglycoproteins varying in oligosaccharide chain length, loading, and carrier protein.
Chem Eur J 7:4411
43. Paoletti LC, Kasper DL, Michon F, DiFabio J, Jennings HJ, Tosteson TD, Wessels MR (1992)
Effects of chain length on the immunogenicity in rabbits of group B Streptococcus type III
oligosaccharide-tetanus toxoid conjugates. J Clin Invest 89:203
44. Chernyak A, Kondo S, Wade TK, Meeks MD, Alzari PM, Fournier JM, Taylor RK, Kováč P,
Wade WF (2002) Induction of protective immunity by synthetic Vibrio cholerae hexasaccharide derived from V. cholerae O1 Ogawa lipopolysaccharide bound to a protein carrier. J Infect
Dis 185:950–962
45. Dick WE Jr, Beurret M (1989) A survey and consideration of design and preparation factors.
In: Cruse JM, Lewis RE Jr (eds) Glycoconjugates of bacterial carbohydrate antigens, vol 10.
Krager, Basel, pp 48–114
46. Tietze LF, Arlt M, Beller M, Glüsenkamp KH, Jähde E, Rajewsky MF (1991) Anticancer agents,
15. Squaric acid diethyl ester: a new coupling reagent for the formation of drug biopolymer
conjugates. Synthesis of squaric acid ester amides and diamides. Chem Ber 124:1215–1221
47. Glüsenkamp KH, Drosdziok W, Eberle G, Jähde E, Rajewsky MFZ (1991) Naturforsch C
Biosci 46:498–501
48. Tietze LF, Schröter C, Gabius S, Brinck U, Goerlach-Graw A, Gabius HJ (1991) Conjugation
of p-aminophenyl glycosides with squaric acid diesters to a carrier protein and the use of the
neoglycoprotein in the histochemical detection of lectines. Bioconjug Chem 2:148–153
49. Cohen S, Cohen SG (1966) Preparation and reactions of derivatives of squaric acid. Alkoxy-,
hydroxy-, and aminocyclobutenediones 1. J Am Chem Soc 88:1533–1536
50. Grünefeld J, Bredhauer G, Zinner G (1985) Zur reaktion von quadratsäuredimethylester mit N,
N -disubstituierten hydrazin-derivaten. Arch Pharm (Weinheim) 318:984–988
51. Bergh A, Magnusson BG, Ohlsson J, Wellmar U, Nilsson UJ (2001) Didecyl squarate – a
practical amino-reactive cross-linking reagent for neoglycoconjugate synthesis. Glycoconj J
18:615–621
52. Kamath VP, Diedrich P, Hindsgaul O (1996) Use of diethyl squarate for the coupling of oligosaccharide amines to carrier proteins and characterization of the resulting neoglycoproteins by
MALDI-TOF mass spectrometry. Glycoconj J 13:315–319
53. Hou S-J, Saksena R, Kováč P (2008) Preparation of glycoconjugates by dialkyl squarate chemistry revisited. Carbohydr Res 343:196–210
54. Saksena R, Adamo R, Kováč P (2007) Immunogens related to the synthetic tetrasaccharide
side chain of the Bacillus anthracis exosporium. Bioorg Med Chem 15:4283–4310
55. Bongat AFG, Saksena R, Adamo R, Fujimoto Y, Shiokawa Z, Peterson DC, Fukase K, Vann
WF, Kováč P (2010) Multimeric bivalent immunogens from recombinant tetanus toxin HC
fragment, synthetic hexasaccharides and a glycopeptide adjuvant. Glycoconj J 27:69–77
56. Aebersold R, Mann M (2003) Mass spectrometry-based proteomics. Nature 422:198–207
57. Morelle W, Michalski JC (2005) Glycomics and mass spectrometry. Curr Pharm Des
11:2615–2645
58. Dettmer K, Aronov PA, Hammock BD (2007) Mass spectrometry-based metabolomics. Mass
Spectrom Rev 26:51–78
M. Bologna et al.
39. Avery OT, Goebel WF (1929) Chemo-immunological studies on conjugated carbohydrateproteins. II Immunological specificity of synthetic sugar-protein antigens. J Exp Med
50:533–550
40. Pollard AJ, Perrett KP, Beverley PC (2009) Maintaining protection against invasive bacteria
with protein-polysaccharide conjugate vaccines. Nat Rev 9:213–220
41. Daum RS, Hogerman D, Rennels MB, Bewley K, Malinoski F, Rothstein E, Reisinger K,
Block S, Keyserling H, Steinhoff M (1997) Infant immunization with pneumococcal CRM 197
vaccines: effect of saccharide size on immunogenicity and interactions with simultaneously
administrated vaccines. J Infect Dis 176:445–455
42. Lefeber DJ, Kamerling JP, Vliegenthart JFG (2001) Synthesis of Streptococcus pneumoniae
type 3 neoglycoproteins varying in oligosaccharide chain length, loading, and carrier protein.
Chem Eur J 7:4411
43. Paoletti LC, Kasper DL, Michon F, DiFabio J, Jennings HJ, Tosteson TD, Wessels MR (1992)
Effects of chain length on the immunogenicity in rabbits of group B Streptococcus type III
oligosaccharide-tetanus toxoid conjugates. J Clin Invest 89:203
44. Chernyak A, Kondo S, Wade TK, Meeks MD, Alzari PM, Fournier JM, Taylor RK, Kováč P,
Wade WF (2002) Induction of protective immunity by synthetic Vibrio cholerae hexasaccharide derived from V. cholerae O1 Ogawa lipopolysaccharide bound to a protein carrier. J Infect
Dis 185:950–962
45. Dick WE Jr, Beurret M (1989) A survey and consideration of design and preparation factors.
In: Cruse JM, Lewis RE Jr (eds) Glycoconjugates of bacterial carbohydrate antigens, vol 10.
Krager, Basel, pp 48–114
46. Tietze LF, Arlt M, Beller M, Glüsenkamp KH, Jähde E, Rajewsky MF (1991) Anticancer agents,
15. Squaric acid diethyl ester: a new coupling reagent for the formation of drug biopolymer
conjugates. Synthesis of squaric acid ester amides and diamides. Chem Ber 124:1215–1221
47. Glüsenkamp KH, Drosdziok W, Eberle G, Jähde E, Rajewsky MFZ (1991) Naturforsch C
Biosci 46:498–501
48. Tietze LF, Schröter C, Gabius S, Brinck U, Goerlach-Graw A, Gabius HJ (1991) Conjugation
of p-aminophenyl glycosides with squaric acid diesters to a carrier protein and the use of the
neoglycoprotein in the histochemical detection of lectines. Bioconjug Chem 2:148–153
49. Cohen S, Cohen SG (1966) Preparation and reactions of derivatives of squaric acid. Alkoxy-,
hydroxy-, and aminocyclobutenediones 1. J Am Chem Soc 88:1533–1536
50. Grünefeld J, Bredhauer G, Zinner G (1985) Zur reaktion von quadratsäuredimethylester mit N,
N -disubstituierten hydrazin-derivaten. Arch Pharm (Weinheim) 318:984–988
51. Bergh A, Magnusson BG, Ohlsson J, Wellmar U, Nilsson UJ (2001) Didecyl squarate – a
practical amino-reactive cross-linking reagent for neoglycoconjugate synthesis. Glycoconj J
18:615–621
52. Kamath VP, Diedrich P, Hindsgaul O (1996) Use of diethyl squarate for the coupling of oligosaccharide amines to carrier proteins and characterization of the resulting neoglycoproteins by
MALDI-TOF mass spectrometry. Glycoconj J 13:315–319
53. Hou S-J, Saksena R, Kováč P (2008) Preparation of glycoconjugates by dialkyl squarate chemistry revisited. Carbohydr Res 343:196–210
54. Saksena R, Adamo R, Kováč P (2007) Immunogens related to the synthetic tetrasaccharide
side chain of the Bacillus anthracis exosporium. Bioorg Med Chem 15:4283–4310
55. Bongat AFG, Saksena R, Adamo R, Fujimoto Y, Shiokawa Z, Peterson DC, Fukase K, Vann
WF, Kováč P (2010) Multimeric bivalent immunogens from recombinant tetanus toxin HC
fragment, synthetic hexasaccharides and a glycopeptide adjuvant. Glycoconj J 27:69–77
56. Aebersold R, Mann M (2003) Mass spectrometry-based proteomics. Nature 422:198–207
57. Morelle W, Michalski JC (2005) Glycomics and mass spectrometry. Curr Pharm Des
11:2615–2645
58. Dettmer K, Aronov PA, Hammock BD (2007) Mass spectrometry-based metabolomics. Mass
Spectrom Rev 26:51–78
M. Bologna et al.